CA1332356C - Therapeutic agent delivery system - Google Patents
Therapeutic agent delivery systemInfo
- Publication number
- CA1332356C CA1332356C CA000573269A CA573269A CA1332356C CA 1332356 C CA1332356 C CA 1332356C CA 000573269 A CA000573269 A CA 000573269A CA 573269 A CA573269 A CA 573269A CA 1332356 C CA1332356 C CA 1332356C
- Authority
- CA
- Canada
- Prior art keywords
- therapeutic agent
- delivery system
- agent
- silicone oil
- centipoise
- 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.)
- Expired - Fee Related
Links
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
- A61K9/0024—Solid, semi-solid or solidifying implants, which are implanted or injected in body tissue
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
- A61K9/5005—Wall or coating material
- A61K9/5021—Organic macromolecular compounds
- A61K9/5031—Organic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyethylene glycol, poly(lactide-co-glycolide)
Abstract
Abstract of the Disclosure A therapeutic agent delivery system that includes a biodegradable polymer and a therapeutic agent, the delivery system being coated with a barrier substance that decreases the quantity of the agent released from the system, compared to the quantity of the agent released from a system not coated with the substance, in the forty-eight hours subsequent to the parenteral injection or implantation of the system into a living person or animal.
Description
133~35~
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Therapeutic Aqent Delivery SYstem Backqround of the Invention This invention relates to the release of therapeutic agents from delivery systems.
Biodegradable polymers containing a therapeutic agent are often used to administer the agent to a patient. Generally the release results from the dissolution of the polymer and from the diffusion of the agent through pores and channels in the matrix.
SummarY of the Invention In general~ the invention features, in one aspect, a therapeutic agent delivery system that includes a biodegradable polymer and a therapeutic agent, the delivery system being coated with a barrier substance that decreases the quantity of the agent released from the system, compared to the quantity of the agent released from a system not coated with the substance, in the forty-eight hours subsequent to the parenteral injection or implantation of the matrix into a living person or animal.
In preferred embodiments, the barrier subs~ance is silicone oil that has a viscosity of between lo2 centipoise (cp) and 104 cp.
~`In another aspect, the invention features a method of providing a coated therapeutic agent delivery system that includes a biodegradable polymer and a therapeutic agent, the method including the steps of coating the delivery system with a barrier substance, and trea~ing the delivery system to remove some but not all of the barrier substance.
In some pre~erred embodiments, the barrier substance is a silicone oil, and the treating includes . ~
,::
13323~6 washing the delivery system with a solvent that removes some of the barrier substance.
Delivery systems consisting of a biodegradable polymer and a therapeutic agent are made in a variety of ways, e.g., solvent casting, coacervation procedures, or dispersion. When the former procedure is used, the agent is dispersed as small particles throughout the system. The small particles are irregularly shaped with small jagged edges; the edges may extend to the surface of the system, or may cause cracks in the system that extend to the surface. When such a system is ; inserted into a patient, a dose of agent larger than the desired dosage is released from the system through these surface contacts.
Delivery systems prepared by coacervation consist of an aggregate of agent surrounded by the polymer. The large crystal may have jagged edges extending to the surface, or may cause cracks that extend to the surface. Accordingly, the initial burst of agent problem is also present in these systems.
. Coating the surface of t~ delivery system with a barrier substance limits the release of agent from the de~livery system for the initial one or two day period following administration, thus decreasing the agent's possible deleterious side effects that can result from initial bursts of high agent release. In addition, ~ because the initial quantity of agent released is j limited, more agent remains in the system allowing for a ' longer effective period of use for the matrix. .
The delivery system is easy to use and inexpensive to make. Moreover, ~ecause of the coating, , - ~
the delivery system has superior handling properties in that it does not clump together when in powdered form.
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Other features and advantages of the invention will.be apparent from the following description of the prefereed embodiment, and from the claims.
Descri~tion of the Preferred Embodiment We now describe the structure, method of preparation, and use of the preferred embodiment.
Structure The delivery system employs a biodegradable polymer containing a therapeutic agent. The system is coated with a barrier substance; the barrier substance, when the system is introduced into a vertebrate (preferably a mammal such as a human or domestic animal such as a dog or cow) decreases the initial burst of therapeutic agent from the system.
A biodegradable polymer is a polymer which slowly dissolves or degrades in a physiological ~: environment into low molecular weight molecules that are then transported from the site. Types of biodegradable polymers suitabIe for use in a delivery system include polyanhydrides, partially crosslinked proteins, polylactic acid, polyglycolic acid, polyorthoesters, polysaccharides, polaxomers, hydroxypropylcellulose, polyethyleneglycol, copolymers of lactide and glycolide, -~ and carboxymethylcellulose. Some representative examples of poly~lactide/glycolide) biodegradable polymers~are described by Kitchell & Wise, 1l2 Methods In Enzymology 436 (1985).
~-~ The delivery sysytems of the invention :i ' preferably are injected or implanted parenterally into an animal or a human patient. Where the system is to be injected, it should be small enough in diameter to fit through the needle tip of the syringe. The preferred deli~ery systems for injection have an average size of 500 microns or less (more preferably 250 microns or , ~
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less, most prefereably 100 or 200 microns); rod shaped systems of 1-10 mm diameter, which generally are long and slender, may also be used.
The term therapeutic agent, as used herein, means any agent used to treat or prevent any disease or disorder of the body. Representative agents include hormones (and hormone fragments and analogues), e.g., testosterone, luteinizing hormone-releasing hormone (LHRH); diuretics, e.g., chlorothiazide;
anti-inflammatories; pain killers, e.g., morphine;
antibiotics, e.g., tetracycline; antipsychotic drugs;
anticancer drugs, e.g., methotrexate, actinomycin D, vinblastine, and cytosine arabinoside; vaccines; and antiarthritic drugs, e.g., ibuprofen and flurbiprofen.
One of the roles of the barrier substance is to limit the initial burst of therapeutic agent from the delivery sys~em. The substance should not affect the long term sustained release of the agent, and therefore should be a substance that dissolves or wears off the surface of the system within a short period of time after injection; preerably, the barrier substance should dissipate within 5 days after injection, more preferably within 2 days after injection. The substance should be non-toxic, non-irritating, non-sensitizing, -~
~ 25 and hydrophobic. Preferably the substance is on the -~ GRAS list or is USP approved.
Examples of suitable barrier substances include paraffins, beeswax, and, preferably, silicone oils.
,~ j ' ~, , ,~ .
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Silicone oils are organo-siloxane polymers base~ on a structure consisting of alterating silicon and oxygen atoms with organic groups (R) attached to the silicon atoms:
R R R
-$io-$i-o$i-R R R
Typical silicone oils include those in which R is a lower alkyl group having six or less carbons, e.g., a methyl group. Silicone oils have a viscosity of between 1 cp and 106cp, The more preferred silicone oils have a viscosity of between 102 cp and 104 cp; most preferably the silicone oils have a viscosity of between 500 cp and 2000 cp. Representative examples of silicone oils include Union Carbide dimethylpolysilicone #L-45 (viscosity looO cp), Dow Corning medical grade silicone oil #360, Aldrich silicone oil (catalogue no. 17,563-3), and Aldrich silicone oil (catalogue no. 14,615-3).
The delivery system can comprise up to 70%
agent by weight. If a system comprises greater than 70%
agent by weight, the mechanical properties of the system may be adversely affected.
Method of Preparation The uncoated delivery system can be prepared by standard solvent casting techniques. In general, the polymer is dissolved in an organic solvent and the therapeutic agent added. The so.ution or suspension is then poured into a suitable mold and the solvent evaporated to`yield a polymer-agent combination.
. 30 Alternatively, the agent can be dispersed with the polymer without soivent.
The delivery systems can also be prepared by coacervation procedures, such as those described by ~' ,~
Lapka et al., Uni~ed States Pat. No. 4,622,244.
The uncoated delivery system of choice ~generally in the form of a powder) iB placed in a flask and covered with a silicone oil such as Union Carbide dimethylpolysillcone #L-45. The thlckness of the coating can be ad~usted by rinsing wlth hexane or other organic ~olvent capable of dissolving silicone oil. The thicker the coating, the more limited the initial burst of release of agent from the system. The powder is dried under a stream of nitrogen gas, and then under vacuum for 24 hour~.
Alternate methods of coating include spraying a thin coat of silicone oil onto the powder, and mixing the powder in a solvent in which the barrier substance has been dissolved and then evaporating off the solvent.
Where the delivery system 1B a powder made up of particles havlng an average size 100-200 microns, following coating each particle should be 0.5%-10~ (more preferably 0.1%-2%) silicone oil by weight. The amount of silicone oil present can be calculated by first conducting an elemental analysis of the powder to determine the amount of silicon present; knowing the percentage of silicon in the oil, the amount of oll can then be determined.
Use The delivery systems containing the standard dosage of the selected therapeutic agent and coated with a barrier substance are in~ected, implanted, or otherwise inserted parenterally into a patient. The barrier substance limits the initial burst of the agent from the polymer; over a short period of time, the barrier substance wears off of the surface of the ~ X
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system, allowing the system to release the desired dosage over a sustained period of time.
A comparison of the initial quantity of agent released from the coated delivery system and an uncoated delivery system can be made by (1) injecting or implanting equal amounts (uncoated weight) of the systems into different animals; and (2) either determining the levels of agent in the animal's blood after 48 hours, or measuring the biological effect that the agent induces (e.g., for delivery systems that release LHRH, the level of testosterone in serum is measured, that level being directly correlated to the a~,ount of LHRH released). It is understood that, although it is most preferred that the initial release be limited to the desired dosage of the agent, the :~ advantages of the invention, such as reducing side effects of large dosages of the agent, are achieved if ~: the initial release is reduced by as little as ten percent (more preferably twenty percent~. -.
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138lR
Therapeutic Aqent Delivery SYstem Backqround of the Invention This invention relates to the release of therapeutic agents from delivery systems.
Biodegradable polymers containing a therapeutic agent are often used to administer the agent to a patient. Generally the release results from the dissolution of the polymer and from the diffusion of the agent through pores and channels in the matrix.
SummarY of the Invention In general~ the invention features, in one aspect, a therapeutic agent delivery system that includes a biodegradable polymer and a therapeutic agent, the delivery system being coated with a barrier substance that decreases the quantity of the agent released from the system, compared to the quantity of the agent released from a system not coated with the substance, in the forty-eight hours subsequent to the parenteral injection or implantation of the matrix into a living person or animal.
In preferred embodiments, the barrier subs~ance is silicone oil that has a viscosity of between lo2 centipoise (cp) and 104 cp.
~`In another aspect, the invention features a method of providing a coated therapeutic agent delivery system that includes a biodegradable polymer and a therapeutic agent, the method including the steps of coating the delivery system with a barrier substance, and trea~ing the delivery system to remove some but not all of the barrier substance.
In some pre~erred embodiments, the barrier substance is a silicone oil, and the treating includes . ~
,::
13323~6 washing the delivery system with a solvent that removes some of the barrier substance.
Delivery systems consisting of a biodegradable polymer and a therapeutic agent are made in a variety of ways, e.g., solvent casting, coacervation procedures, or dispersion. When the former procedure is used, the agent is dispersed as small particles throughout the system. The small particles are irregularly shaped with small jagged edges; the edges may extend to the surface of the system, or may cause cracks in the system that extend to the surface. When such a system is ; inserted into a patient, a dose of agent larger than the desired dosage is released from the system through these surface contacts.
Delivery systems prepared by coacervation consist of an aggregate of agent surrounded by the polymer. The large crystal may have jagged edges extending to the surface, or may cause cracks that extend to the surface. Accordingly, the initial burst of agent problem is also present in these systems.
. Coating the surface of t~ delivery system with a barrier substance limits the release of agent from the de~livery system for the initial one or two day period following administration, thus decreasing the agent's possible deleterious side effects that can result from initial bursts of high agent release. In addition, ~ because the initial quantity of agent released is j limited, more agent remains in the system allowing for a ' longer effective period of use for the matrix. .
The delivery system is easy to use and inexpensive to make. Moreover, ~ecause of the coating, , - ~
the delivery system has superior handling properties in that it does not clump together when in powdered form.
:
:
:
',~
'' ~ ' ' 13323~
Other features and advantages of the invention will.be apparent from the following description of the prefereed embodiment, and from the claims.
Descri~tion of the Preferred Embodiment We now describe the structure, method of preparation, and use of the preferred embodiment.
Structure The delivery system employs a biodegradable polymer containing a therapeutic agent. The system is coated with a barrier substance; the barrier substance, when the system is introduced into a vertebrate (preferably a mammal such as a human or domestic animal such as a dog or cow) decreases the initial burst of therapeutic agent from the system.
A biodegradable polymer is a polymer which slowly dissolves or degrades in a physiological ~: environment into low molecular weight molecules that are then transported from the site. Types of biodegradable polymers suitabIe for use in a delivery system include polyanhydrides, partially crosslinked proteins, polylactic acid, polyglycolic acid, polyorthoesters, polysaccharides, polaxomers, hydroxypropylcellulose, polyethyleneglycol, copolymers of lactide and glycolide, -~ and carboxymethylcellulose. Some representative examples of poly~lactide/glycolide) biodegradable polymers~are described by Kitchell & Wise, 1l2 Methods In Enzymology 436 (1985).
~-~ The delivery sysytems of the invention :i ' preferably are injected or implanted parenterally into an animal or a human patient. Where the system is to be injected, it should be small enough in diameter to fit through the needle tip of the syringe. The preferred deli~ery systems for injection have an average size of 500 microns or less (more preferably 250 microns or , ~
., .: ~
''"" ~
,..
13323~
less, most prefereably 100 or 200 microns); rod shaped systems of 1-10 mm diameter, which generally are long and slender, may also be used.
The term therapeutic agent, as used herein, means any agent used to treat or prevent any disease or disorder of the body. Representative agents include hormones (and hormone fragments and analogues), e.g., testosterone, luteinizing hormone-releasing hormone (LHRH); diuretics, e.g., chlorothiazide;
anti-inflammatories; pain killers, e.g., morphine;
antibiotics, e.g., tetracycline; antipsychotic drugs;
anticancer drugs, e.g., methotrexate, actinomycin D, vinblastine, and cytosine arabinoside; vaccines; and antiarthritic drugs, e.g., ibuprofen and flurbiprofen.
One of the roles of the barrier substance is to limit the initial burst of therapeutic agent from the delivery sys~em. The substance should not affect the long term sustained release of the agent, and therefore should be a substance that dissolves or wears off the surface of the system within a short period of time after injection; preerably, the barrier substance should dissipate within 5 days after injection, more preferably within 2 days after injection. The substance should be non-toxic, non-irritating, non-sensitizing, -~
~ 25 and hydrophobic. Preferably the substance is on the -~ GRAS list or is USP approved.
Examples of suitable barrier substances include paraffins, beeswax, and, preferably, silicone oils.
,~ j ' ~, , ,~ .
~ .
:
',' " ~
~ `
Silicone oils are organo-siloxane polymers base~ on a structure consisting of alterating silicon and oxygen atoms with organic groups (R) attached to the silicon atoms:
R R R
-$io-$i-o$i-R R R
Typical silicone oils include those in which R is a lower alkyl group having six or less carbons, e.g., a methyl group. Silicone oils have a viscosity of between 1 cp and 106cp, The more preferred silicone oils have a viscosity of between 102 cp and 104 cp; most preferably the silicone oils have a viscosity of between 500 cp and 2000 cp. Representative examples of silicone oils include Union Carbide dimethylpolysilicone #L-45 (viscosity looO cp), Dow Corning medical grade silicone oil #360, Aldrich silicone oil (catalogue no. 17,563-3), and Aldrich silicone oil (catalogue no. 14,615-3).
The delivery system can comprise up to 70%
agent by weight. If a system comprises greater than 70%
agent by weight, the mechanical properties of the system may be adversely affected.
Method of Preparation The uncoated delivery system can be prepared by standard solvent casting techniques. In general, the polymer is dissolved in an organic solvent and the therapeutic agent added. The so.ution or suspension is then poured into a suitable mold and the solvent evaporated to`yield a polymer-agent combination.
. 30 Alternatively, the agent can be dispersed with the polymer without soivent.
The delivery systems can also be prepared by coacervation procedures, such as those described by ~' ,~
Lapka et al., Uni~ed States Pat. No. 4,622,244.
The uncoated delivery system of choice ~generally in the form of a powder) iB placed in a flask and covered with a silicone oil such as Union Carbide dimethylpolysillcone #L-45. The thlckness of the coating can be ad~usted by rinsing wlth hexane or other organic ~olvent capable of dissolving silicone oil. The thicker the coating, the more limited the initial burst of release of agent from the system. The powder is dried under a stream of nitrogen gas, and then under vacuum for 24 hour~.
Alternate methods of coating include spraying a thin coat of silicone oil onto the powder, and mixing the powder in a solvent in which the barrier substance has been dissolved and then evaporating off the solvent.
Where the delivery system 1B a powder made up of particles havlng an average size 100-200 microns, following coating each particle should be 0.5%-10~ (more preferably 0.1%-2%) silicone oil by weight. The amount of silicone oil present can be calculated by first conducting an elemental analysis of the powder to determine the amount of silicon present; knowing the percentage of silicon in the oil, the amount of oll can then be determined.
Use The delivery systems containing the standard dosage of the selected therapeutic agent and coated with a barrier substance are in~ected, implanted, or otherwise inserted parenterally into a patient. The barrier substance limits the initial burst of the agent from the polymer; over a short period of time, the barrier substance wears off of the surface of the ~ X
IF ? ~
~`' ' '` ' ",`~ .:' ~.
~'`~' ' ' . ' ' ~' '' ` :
.' 133235~
system, allowing the system to release the desired dosage over a sustained period of time.
A comparison of the initial quantity of agent released from the coated delivery system and an uncoated delivery system can be made by (1) injecting or implanting equal amounts (uncoated weight) of the systems into different animals; and (2) either determining the levels of agent in the animal's blood after 48 hours, or measuring the biological effect that the agent induces (e.g., for delivery systems that release LHRH, the level of testosterone in serum is measured, that level being directly correlated to the a~,ount of LHRH released). It is understood that, although it is most preferred that the initial release be limited to the desired dosage of the agent, the :~ advantages of the invention, such as reducing side effects of large dosages of the agent, are achieved if ~: the initial release is reduced by as little as ten percent (more preferably twenty percent~. -.
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Claims (12)
1. A therapeutic agent delivery system comprising a biodegradable polymer and a therapeutic agent, said delivery system being coated with a barrier substance that decreases the quantity of said agent released from said system, compared with the quantity of said agent released from a said system not coated with said substance, in the forty-eight hours subsequent to the parenteral injection or implantation of said system into a living person or animal.
2. The therapeutic agent delivery system of claim 1 wherein said barrier substance is a silicone oil.
3. The therapeutic agent release system of claim 2 wherein said silicone oil has a viscosity of between 102 centipoise and 104 centipoise.
4. The therapeutic agent release system of claim 3 wherein said silicone oil has a viscosity of between 500 centipoise and 2000 centipoise.
5. Use of a therapeutic agent delivery system according to any one of claims 1 to 4 for administering a therapeutic agent to a vertebrate.
6. Use according to claim 5 wherein said barrier substance is a silicone oil.
7. Use according to claim 6 wherein said silicone oil has a viscosity of between 102 centipoise and 104 centipoise.
8. Use according to claim 7 wherein said silicone oil has a viscosity of between 500 centipoise and 2000 centipoise.
9. Use according to claim 6 wherein said vertebrate is a human.
10. A method of providing a coated therapeutic agent delivery system comprising: coating a therapeutic agent delivery system comprising a biodegradable polymer and a therapeutic agent with a barrier substance that decreases the quantity of said agent released from said system, compared with the quantity of said agent released from a said system not coated with said substance, in the forty-eight hours subsequent to the parenteral injection or implantation of said system into a living person or animal; and removing some but not all of said barrier substance from said delivery system.
11. The method of claim 10 wherein said barrier substance is a silicone oil.
12. The method of claim 10 wherein said treating comprises washing said delivery system with a solvent.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/078,534 US4894231A (en) | 1987-07-28 | 1987-07-28 | Therapeutic agent delivery system |
| US078,534 | 1987-07-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1332356C true CA1332356C (en) | 1994-10-11 |
Family
ID=22144643
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000573269A Expired - Fee Related CA1332356C (en) | 1987-07-28 | 1988-07-28 | Therapeutic agent delivery system |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4894231A (en) |
| EP (1) | EP0301856B1 (en) |
| JP (1) | JP2714415B2 (en) |
| AT (1) | ATE122879T1 (en) |
| CA (1) | CA1332356C (en) |
| DE (1) | DE3853853T2 (en) |
| ES (1) | ES2074050T3 (en) |
| WO (1) | WO1989000839A1 (en) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3279996A (en) * | 1962-08-28 | 1966-10-18 | Jr David M Long | Polysiloxane carrier for controlled release of drugs and other agents |
| US3854480A (en) * | 1969-04-01 | 1974-12-17 | Alza Corp | Drug-delivery system |
| BE791632A (en) * | 1971-11-20 | 1973-05-21 | Schering Ag | SILICONIC RUBBER-BASED SUPPORTS FOR MEDICINAL PRODUCTS |
| CA1045977A (en) * | 1973-05-17 | 1979-01-09 | Arthur D. Little | Biodegradable, implantable drug delivery device, and process for preparing and using the same |
| US4351337A (en) * | 1973-05-17 | 1982-09-28 | Arthur D. Little, Inc. | Biodegradable, implantable drug delivery device, and process for preparing and using the same |
| US3944064A (en) * | 1973-10-26 | 1976-03-16 | Alza Corporation | Self-monitored device for releasing agent at functional rate |
| DE2824112A1 (en) * | 1978-06-01 | 1979-12-06 | Garching Instrumente | Micro-pellets of biodegradable polymeric carrier - esp. poly:hydroxy-carboxylic acid, and active ingredient e.g. narcotic antagonist |
| US4159322A (en) * | 1978-06-26 | 1979-06-26 | A. H. Robins Company, Inc. | Anticoccidium implants |
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| EP0321457A1 (en) * | 1986-01-13 | 1989-06-28 | Research Corporation | Aqueous dispersions of waxes and lipids for pharmaceutical coating |
| IT1200217B (en) * | 1986-09-30 | 1989-01-05 | Valducci Roberto | MEMBRANE FOR PHARMACEUTICAL AND INDUSTRIAL USE |
-
1987
- 1987-07-28 US US07/078,534 patent/US4894231A/en not_active Expired - Fee Related
-
1988
- 1988-07-27 JP JP63507102A patent/JP2714415B2/en not_active Expired - Lifetime
- 1988-07-27 WO PCT/US1988/002546 patent/WO1989000839A1/en unknown
- 1988-07-28 DE DE3853853T patent/DE3853853T2/en not_active Expired - Fee Related
- 1988-07-28 ES ES88306958T patent/ES2074050T3/en not_active Expired - Lifetime
- 1988-07-28 EP EP88306958A patent/EP0301856B1/en not_active Expired - Lifetime
- 1988-07-28 CA CA000573269A patent/CA1332356C/en not_active Expired - Fee Related
- 1988-07-28 AT AT88306958T patent/ATE122879T1/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| WO1989000839A1 (en) | 1989-02-09 |
| JPH02500521A (en) | 1990-02-22 |
| EP0301856B1 (en) | 1995-05-24 |
| DE3853853D1 (en) | 1995-06-29 |
| ATE122879T1 (en) | 1995-06-15 |
| EP0301856A3 (en) | 1990-07-25 |
| EP0301856A2 (en) | 1989-02-01 |
| US4894231A (en) | 1990-01-16 |
| DE3853853T2 (en) | 1995-12-07 |
| ES2074050T3 (en) | 1995-09-01 |
| JP2714415B2 (en) | 1998-02-16 |
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