GB2091554A - Rod-like Moulded Drug - Google Patents
Rod-like Moulded Drug Download PDFInfo
- Publication number
- GB2091554A GB2091554A GB8200711A GB8200711A GB2091554A GB 2091554 A GB2091554 A GB 2091554A GB 8200711 A GB8200711 A GB 8200711A GB 8200711 A GB8200711 A GB 8200711A GB 2091554 A GB2091554 A GB 2091554A
- Authority
- GB
- United Kingdom
- Prior art keywords
- drug
- molded
- rods
- living body
- acid
- 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
- 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
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/2027—Organic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone, poly(meth)acrylates
-
- 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
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/2031—Organic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyethylene glycol, polyethylene oxide, poloxamers
- A61K9/204—Polyesters, e.g. poly(lactide-co-glycolide)
Landscapes
- Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Dermatology (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The present invention relates to a moulded drug comprising a mixture of a high-molecular material absorbable in the living body and a medicine which drug is in the form of rods substantially capable of piercing the living body. The moulded drug is to be pierced in an affected part of the living body of a patient suffering from, for example, cancer, whereby the medicine is gradually released to kill the cancer cells.
Description
SPECIFICATION
New Molded Drug
The present invention relates to a new rod-shaped drug substantially capable of being pierced in a living body as a whole. An object of the present invention is to provide a new drug delivery system for drugs to be applied locally to an affected part of patient.
Recently, studies are made intensively on an administration method in which a drug is given continuously to an affected part or around the part of a patient having local tumor or cancer for a long period of time. For the controlled-release administration by the local application of a drug, there have been known various methods such as a method wherein capsules containing a drug are embedded around an affected part, a method wherein a drug is shaped into tablets or pellets using an excipient such as a resin, if necessary, and they are embedded around an affected part a method wherein a drug is treated with a capsule-forming agent by a process known per se, the thus obtained micro-capsules containing the drug are injected in a muscle or blood vessel around an affected part so that the capsules stay in the capillary vessels near the affected part to allow the drug to exude from the capsules.
However, the embedding around an affected part requires a surgical operation and parts in which the embedding is possible are limited. When powders or pellets molded by using an excipient are made fluid and directly injected in the body by means of, for example, an injector, it is difficult to deeply embed them in the affected part, though the surgical operation is not required. An essential defect of the micro-capsule method has been pointed out that the micro-capsules staying in a blood vessel inevitably inhibit the blood circulation resulting in necrosis around it. Defects of both methods are that a capsule-forming material or fixing polymer material remains in the body. The high-molecular material remaining in the body for a long period of time would exert some influences on the living body.
After intensive investigations on new administration methods of drugs made under these circumstances, the inventors have attained to the present invention.
A term "high-molecular material absorbable in living body" herein indicates a high-molecular material which is decomposed under vital conditions in the body, such as enzymes and body temperature or combination of many other factors occurring in the body, into metabolites which are harmless to the living body and which are absorbed in the living body or excreted therefrom by functions peculiar to the living body. Those high-molecular materials may be chemically synthesized or they may be obtained from materials occurring in living bodies or they may be a combination thereof.
As the chemically synthesized high-molecular materials, there may be mentioned, for example, polyglycolic acid, polylactic acid, glycolic acid/lactic acid copolymer and compositions comprising them as well as polyalkyl cyanoacrylates. As the materials occurring in living bodies, there may be mentioned, for example, soluble collagen and oxidized cellulose. They may be used also in the form of a mixture thereof. However, high-molecular materials which are synthesized completely chemically and which are absorbable in a living body are desirable for shaping them into rods capable of being pierced in the living body to attain the characteristic feature of the present invention.
Particularly preferred materials are aliphatic polyesters. It has been known that those esters are absorbed in the living body in a harmless form or excreted. Polyglycolic acid and polylactic acid have a high compression strength and, therefore, even if they are molded into needle-shaped rods they still have a stength sufficient for the piercing into the body. Rods having a compression strength sufficient for the piercing in the living body can be obtained from the glycolic acid/lactic acid copolymer by selecting glycolic acid/lactic acid ratio in the copolymer according to the size of the rods.In glycolic acid homopolymers and copolymers, glycolic acid content is preferably 100--80 wt. %. In lactic acid homopolymers and copolymers, lactic acid content is preferably 100--90 wt. %. As the polyglycolic acid, those having a low polymerization degree and an intrinsic viscosity of about 0.2 (determined in a solution comprising 7 parts by weight of trichlorophenol and 10 parts by weight of phenol at 300 C) are usable. From the viewpoint of the molding operation, those having an intrinsic viscosity of up to 0.9 are preferred. The lactic acid homopolymers and copolymers have a degree of crystallinity of preferably at least 30% in the form of rods.
The drugs used in the present invention are preferably those which can directly be applied to parts around the affected part such as carcinostatics, hormones, insulin, local analgesics and antibiotics.
The carcinostatics used in the present invention include antimetabolites such as 5-FU, THFU and cytarabine, alkylating agents such as carmustine and nimumstine (nidran), and anticarcinogenic antibiotics such as mitomycin, carzinophilin, adriamycin and bleomycin.
As other medical administration systems in which the rods of the present invention are used, there may be mentioned local anesthesia and X-ray projection. Anesthetics and contrast media used in those systems are also included in the present invention. Further, other drugs may be used in the present invention without any particular limitation.
Ratio-of the high-molecular material absorbable in the living body to the drug in the molded composition according to the present invention is preferably 30-99 parts by weight to 70-1 part by weight. The ratio is determined depending on active ingredient-reieasing rate required, dose, period and size and strength of the molded composition of the present invention and also according to purpose of the administration.
The present invention provides a molded carcinostatic drug of controlled release type which comprises 1-70 wt. %, based on an aliphatic polyester absorbable in the living body, of a carcinostatic agent and which is to be pierced in a part affected by cancer. The rod-shaped carcinostatic drug of controlled release type capable of being pierced directly in the body is obtained by selecting an aliphatic polyester which is harmless to the living body and decomposed and absorbed in the living body and has excellent physical properties, particularly a high compression strength as the high-molecular material for fixing the drug and also specifically selecting the drug content of the molded product.
For obtaining the rod-shaped drug substantially capable of piercing into the living body without using any plunger according to the present invention, for example, cylindrical rods having a diameter of about 1.5-2 mm should have a compression strength of preferably at least 200 g when the length in 1 cm.
The present invention is characterized in that a mixture of the high-molecular material absorbable in the living body and the medicine is molded into rods capable of piercing in the body. The term "rods substantially capable of piercing into the living body" herein indicates rods including needle-like rods having a diameter of up to about 2 mm and rods obtained by cutting a molded plate of a given thickness into rods of a suitable width of up to about 5 mm according to a width of the affected part in which they are to be inserted. A preferred shape of the rods is a needle-like shape. If necessary, an end of each rod may be sharpened so that it can be pierced around or in an affected part directly or by means of a plunger or the like in the same manner as in the acupuncture and moxibustion.When the needle-like molded product having a diameter of up to 2 mm is to be produced, it is desirable to select polyglycolic acid having a quite high compression strength as the high-molecular material absorbable in the living body According to the period in which the active ingredient is to be released gradually and amount of the active ingredient, a combination of rods having different diameters and lengths may be employed or plates having different thicknesses and lengths selected may be cut into the rods.
The length of the rods varies depending on the affected part in which they are to be pierced. Rods to be pierced in organs in the body have lengths ranging from about 1 cm to about 5 cm (toothpickshaped rods).
The molded drugs of the present invention may be obtained by various ordinary methods of molding high-molecular materials. The method is selected suitably depending on the purpose to form rods or plates. For example, the method is suitably selected from melt spinning, compression molding, injection molding, transfer molding, casting and sintering molding methods. The drug is mixed with the high-molecular material absorbable in the living body by melting at a temperature below a decomposition temperature of the drug or the drug is mixed with said high-molecular material dissolved in a solvent and the mixture is then molded.If a high-molecular monomer easily polymerizable into the high-molecular material absorbable in the living body can be used for the production of the molded drug, the high-molecular monomer is mixed with the drug, and then the mixture is charged in a mold to carry out the polymerization by a proper polymerization-initiation method to obtain the intended molded drug. However, the method wherein a solvent is used in the molding step or the method wherein a monomer is polymerized to obtain a molded product is not preferred, since the removal of the solvent from the molded drug or the removal of the unreacted monomer is difficult. In order to distribute the active ingredient uniformly in the high-molecular base absorbable in the living body, it is desirable to homogeneously mix the active ingredient powder with the powder base before the melting by heating.
The drug thus molded into rods contains the high-molecular material which is absorbable in the living body and which has a relatively high compression molding and it does not always require the use of a plunger such as an injector or surgical operation for the piercing. The rods can be administered to an affected part of patient accurately and easily substantially without causing bleeding. Accordingly, the active ingredient in a high concentration acts on the affected part in only a limited area. Particularly in case the surgical operation is impossible in the treatment of cancers in the organs such as a liver, the rod-shaped drug of the present invention can be pierced therein to effect the therapy.If a small amount of X-ray contrast medium is incorporated in the drug in addition to a carcinostatic or the like, it is possible to confirm the cite of the piercing according to roentgenoscopy at the time of the administration. Further, the dose can be maintained or controlled in a deep, affected part by previously determining the active ingredient content of the rod and concentration thereof to be gradually released, since the drug of the present invention is molded into rods having uniform shape and a given active ingredient content. The following examples will illustrate the present invention.
Example 1
100 parts by weight of glycolic acid/lactic acid polymer (50:50) passed through a 60 mesh sieve was mixed homogeneously with 50 parts by weight of finely pulverized 5-fluorouracil (a product of
Mitsui Seiyaku Co.) to obtain a composition. The composition was molded into rods having a diameter of 1 mm by means of a Koka type flow tester (a product of Shimazu Seisakusho) at 1800 C.
The molded product having a length of 1 cm had a compression strength in the longitudinal direction of 320 g.
Example 2
100 parts of polyethyl cyanoacrylate obtained by polymerizing ethyl cyanoacrylate monomer commercially available as an adhesive for the surgical operation by casting in a petri dish was dissolved in 1000 parts by weight of acetone. 50 parts by weight of finely pulverized 50 fluorouracil was dispersed in the solution and the whole was poured in a petri dish to obtain a plate by casting method.
The plate was dried at 1000C in vacuum for 24 hours to completely remove acetone therefrom.
The thus obtained plate having a thickness of 0.1 mm was cut into rods. The rods had a compression strength of 270 g, when determined in the same manner as in Example 1.
Example 3
100 parts by weight of polyglycolic acid (having an intrinsic viscosity in a mixed solution of 7 parts by weight of trichlorophenol and 10 parts by weight of phenol at 300C of 0.3) passed through a 60 mesh sieve was mixed with 30 parts by weight of finely pulverized 5-fluorouracil in a constant temperature bath at 21 00C to obtain a solution. Rods having a diameter of 1 mm were prepared from the solution by the crystal pulling method.
The rods had a compression strength in the longitudinal direction of 750 g/cm.
Example 4
100 parts of ethyl cyanoacrylate monomer was mixed with 30 parts of 5-fluorouracil. The mixture was poured in a glass petri dish at room temperature to obtain a plate having a thickness of 1 mm comprising polyethyl cyanoacrylate and 5-fluorourcil. The plate was cut into rods having a diameter of 1 mm. The rods having a length of 1 cm had a compression strength in the longitudinal direction of 640 g.
Example 5
30 parts by weight of polyglycolic acid (the same as that used in Example 3) was mixed with 70 parts by weight of glycolic acid/lactic acid copolymer (50:50; the same as that used in Example 1). The mixture was dissolved in a solution of resin in chloroform. A chemical shown in Table 1 was added to the resulting solution and the whole was poured in a needle-shaped mold. The solvent was vaporized to obtain needle-shaped molded product having a diameter of 2 mm. It had a compression strength in the longitudinal direction (1 cm length) as shown in Table 1.
Table 1
Amount Compression strength (in total of the molded
Active ingredient 50 mg} product
1 -(2-Tetrahydrofuryl)
5-fluorourcil
(carcinostatic) 1 5 mg 740 g
Mitomycin C
(carcinostatic) 1 5 mg 750 g
Ilosone
(carcinostatic) 20 mg 250 g
Example 6
100 parts by weight of polyglycolic acid (having an intrinsic viscosity in a mixed solution of 7 parts by weight of trichlorophenol and 10 parts by weight of phenol at 300C of 0.3) passed through a 60 mesh sieve was mixed homogeneously with 30 parts by weight of finely pulverized 5-fluorourcil.
The mixture was treated in a constant temperature bath at 21 00C to obtain a solution. Rods having a diameter of 1 mm were prepared from the solution by the crystal pulling method.
The rods having a length of 1 cm had a compression strength in the longitudinal direction of 750 g.
Example 7
100 parts by weight of glycolic acid/lactic acid copolymer (comprising 80 wt. % of glycolic acid and 20 wt. % of lactic acid) passed through a 60 mesh sieve was homogeneously mixed with 50 parts by weight of finely pulverized mitomycin (a product of Sankyo Co.). The mixture was molded into rods having a diameter of 1 mm by means of a Koka type fiow tester (a product of Shimazu Seisakusho) at 1800C.
The rods had a compression strength in the longitudinal direction of 380 g as determined by using samples having a length of 1 cm.
Test 1
A controlled release effect of 5-fluorourcil rods prepared using polyglycolic acid in Example 6 was examined.
The needle-shaped drug having a length of 1 cm and a diameter of 2 mm (total weight: 50 mg, 5fluorourcil content: 1 6.5 mg) was pierced and completely embedded in the liver of a rat (body weight:
385 g, 1 00 days after the birth). Change in amount of 5-fluorourcil remaining in the polymer base with time was examined to determine the exudation rate of 5-fluorourcil.
The results are shown in Table 1.
Table 1
Amount of 5-phlorouracil
Time (days) remaining (mgj Rate {%J 1 10.73 65
3 6.11 37
5 3.79 23
7 1.82 11
11 0.49 3
15 0 0
Thus, it was recognized that 5-fluorourcil was released gradually over 1 5 days.
5-fluorourcil concentration in the serum of the rat was as low as 0.2-0.02 g/g for 7 days directly after the embedding. It is supposed that the active ingredient in a high concentration acts only on and around an affected part without causing any side effect.
Test 2
Yoshida sarcoma cells were planted in the abdomen of each of two rats weighing 296 g and 340 g, respectively. Two weeks thereafter, a rod containing 5-fluorourcil (having a length of 1 cm, diameter of 1.5 mm, total weight of 20 mg and 5-fluorourcil content of 6.0 mg) obtained by using polyglycolic acid in Example 6 was pierced and embedded in each rat and advance of sarcoma was observed.
The results are shown in Table 2.
Table 2
Condition of
rat before Change after the administration
Rat the admini
No. stration 4 days 8 days 1 1 days 13 days 20 days 296g 303 315 330 332 360
(15x15 mm) (18x14) (14x10) (6x6) (0) (o) II 340 g 340 359 364 376 402
(12x22mm) (15x15) (14x14) (11x11) (6x6) (O) Numerals in the parentheses represent sarcoma diameters.
It is recognized that the disease was completely cured 1 3 days after the administration of the molded drug of the present invention.
Claims (6)
1. A molded drug comprising a mixture of a high-molecular material absorbable in the living body and a medicine which drug is molded into rods substantially capable of piercing in the living body.
2. A molded drug according to Claim 1 wherein the high-molecular material absorbable in the living body is one or more materials selected from the group consisting of polyglycolic acid, polylactic acid, glycolic acid/lactic acid copolymer and polyalkyl cyanoacrylates.
3. A molded drug according to Claim 1 wherein the medicine is that usable for the local administration to an affected part.
4. A molded drug according to Claim 1 wherein the medicine is a carcinostatic medicine.
5. A molded drug according to Claim 1 wherein the rod has a compression strength of at least 200 g when the diameter is 1.5-2 mm and the length is 1 cm.
6. A molded carcinostatic of controlled release type according to Claims 1 to 5 which contains 1-70 wt. %, based on an aliphatic polyester (selected from the group consisting of polyglycolic acid, polyactic acid, and glycolic acid/lactic acid copolymer), of a carcinostatic agent and which has been molded into rods to be pierced in an affected part in the body.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP273781A JPS57116008A (en) | 1981-01-13 | 1981-01-13 | Novel formed drug |
| JP16199881A JPS5865211A (en) | 1981-10-13 | 1981-10-13 | Slow-releasing formed carcinostatic agent |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB2091554A true GB2091554A (en) | 1982-08-04 |
| GB2091554B GB2091554B (en) | 1984-09-12 |
Family
ID=26336200
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB8200711A Expired GB2091554B (en) | 1981-01-13 | 1982-01-11 | Rod like moulded drug |
Country Status (4)
| Country | Link |
|---|---|
| CH (1) | CH650405A5 (en) |
| DE (1) | DE3200763A1 (en) |
| FR (1) | FR2497661B1 (en) |
| GB (1) | GB2091554B (en) |
Cited By (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0139286A2 (en) * | 1983-10-14 | 1985-05-02 | Sumitomo Pharmaceuticals Company, Limited | Prolonged sustained-release preparations |
| EP0268680A1 (en) * | 1986-05-29 | 1988-06-01 | Vsesojuzny Nauchno-Issledovatelsky I Ispytatelny Institut Meditsinskoi Tekhniki | Antitumor film of biodestructible polymers |
| EP0281482A1 (en) * | 1987-03-06 | 1988-09-07 | Research Triangle Institute | Polymer blends for selective biodegradability |
| US4774091A (en) * | 1983-10-14 | 1988-09-27 | Sumitomo Pharmaceuticals Company, Ltd. | Long-term sustained-release preparation |
| US4797287A (en) * | 1984-06-19 | 1989-01-10 | Basf Aktiengesellschaft | Cylindrical microtablets |
| US4849141A (en) * | 1985-12-27 | 1989-07-18 | Sumitomo Pharmaceuticals Company, Limited | Method for producing sustained release formulation |
| US4855134A (en) * | 1983-10-14 | 1989-08-08 | Sumitomo Pharmaceuticals Company, Limited | Sustained-release preparation |
| FR2673843A1 (en) * | 1991-03-14 | 1992-09-18 | Centre Nat Rech Scient | IMPLANTABLE, BIORESORBABLE PHARMACEUTICAL COMPOSITION BASED ON POLY (LACTIC ACID), INTENDED TO IMPLEMENT A LOCAL INTERNAL ANTIBOTHERAPY. |
| US5183662A (en) * | 1990-08-30 | 1993-02-02 | Senju Pharmaceutical Co., Ltd. | Controlled drug release composition |
| US5385738A (en) * | 1983-10-14 | 1995-01-31 | Sumitomo Pharmaceuticals Company, Ltd. | Sustained-release injection |
| WO1996008308A1 (en) * | 1994-09-16 | 1996-03-21 | Angus Chemical Company | Bis-oxazolidines and their use |
| WO1996008289A1 (en) * | 1994-09-12 | 1996-03-21 | Societe De Conseils De Recherches Et D'applications Scientifiques, S.A. | Needle-less parenteral introduction device |
| US5545485A (en) * | 1993-09-14 | 1996-08-13 | Fujitsu Limited | Biodegradable resin molded article |
| FR2770134A1 (en) * | 1998-10-28 | 1999-04-30 | Delab | Device for accurate parenteral implantation of solid formulation |
| WO1999030684A1 (en) * | 1997-12-12 | 1999-06-24 | Supergen, Inc. | Local delivery of therapeutic agents |
| AU745055B2 (en) * | 1994-09-12 | 2002-03-07 | Delab | Parenterally administered medicament |
| US6544545B1 (en) | 1994-09-12 | 2003-04-08 | Societe De Conseils De Recherches Et D'applications Scientifiques, S.A.S. | Needle-less parenteral introduction device |
| EP1159957A3 (en) * | 1996-12-02 | 2003-06-04 | Societe De Conseils De Recherches Et D'applications Scientifiques (S.C.R.A.S.) | Device for the local administration of solid or semi-solid formulations, sustained release formulations for parenteral administration and process of preparation |
| WO2008102136A3 (en) * | 2007-02-22 | 2009-01-15 | Glide Pharmaceutical Technolog | Solid pharmaceutical and vaccine dose |
| US7666844B2 (en) | 1999-04-16 | 2010-02-23 | Novo Nordisk A/S | Dry mouldable drug formulation |
| US7815928B2 (en) | 1996-12-02 | 2010-10-19 | Societe De Conseils De Recherches Et D'applications Scientifiques Scras | Device for local administration of solid or semi-solid formulations and delayed-release formulations for proposal parenteral administration and preparation process |
| ES2362525A1 (en) * | 2009-10-08 | 2011-07-07 | Azurebio, S.L. | Formulation of drugs and vaccines in the form of percutaneous injectable needles |
| US8454997B2 (en) | 2001-12-18 | 2013-06-04 | Novo Nordisk A/S | Solid dose micro implant |
| AU2014253541B2 (en) * | 2007-02-22 | 2016-07-28 | Glide Pharmaceutical Technologies Limited | Solid pharmaceutical and vaccine dose |
| US10596330B2 (en) | 2015-08-26 | 2020-03-24 | Medtronic Xomed, Inc. | Resorbable, drug-eluting submucosal turbinate implant device and method |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102020203106A1 (en) | 2020-03-11 | 2021-09-16 | Lts Lohmann Therapie-Systeme Ag | Active substance stamp with an insert for sudden application |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3887699A (en) * | 1969-03-24 | 1975-06-03 | Seymour Yolles | Biodegradable polymeric article for dispensing drugs |
| US3773919A (en) * | 1969-10-23 | 1973-11-20 | Du Pont | Polylactide-drug mixtures |
| US3857932A (en) * | 1970-09-09 | 1974-12-31 | F Gould | Dry hydrophilic acrylate or methacrylate polymer prolonged release drug implants |
| US4014987A (en) * | 1974-06-04 | 1977-03-29 | Alza Corporation | Device for delivery of useful agent |
| DE2843963A1 (en) * | 1978-10-09 | 1980-04-24 | Merck Patent Gmbh | BODY-RESORBABLE SHAPED MATERIAL BASED ON COLLAGEN AND THEIR USE IN MEDICINE |
| US4249531A (en) * | 1979-07-05 | 1981-02-10 | Alza Corporation | Bioerodible system for delivering drug manufactured from poly(carboxylic acid) |
-
1982
- 1982-01-11 GB GB8200711A patent/GB2091554B/en not_active Expired
- 1982-01-12 CH CH15282A patent/CH650405A5/en not_active IP Right Cessation
- 1982-01-13 DE DE19823200763 patent/DE3200763A1/en active Granted
- 1982-01-13 FR FR8200431A patent/FR2497661B1/en not_active Expired
Cited By (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5021241A (en) * | 1983-10-14 | 1991-06-04 | Sumitomo Pharmaceuticals Company, Limited | Long-term sustained-release preparation |
| EP0139286A3 (en) * | 1983-10-14 | 1985-10-30 | Sumitomo Chemical Company, Limited | Prolonged sustained-release preparations |
| US5385738A (en) * | 1983-10-14 | 1995-01-31 | Sumitomo Pharmaceuticals Company, Ltd. | Sustained-release injection |
| EP0139286A2 (en) * | 1983-10-14 | 1985-05-02 | Sumitomo Pharmaceuticals Company, Limited | Prolonged sustained-release preparations |
| US4774091A (en) * | 1983-10-14 | 1988-09-27 | Sumitomo Pharmaceuticals Company, Ltd. | Long-term sustained-release preparation |
| US4855134A (en) * | 1983-10-14 | 1989-08-08 | Sumitomo Pharmaceuticals Company, Limited | Sustained-release preparation |
| US5081156A (en) * | 1983-10-14 | 1992-01-14 | Sumitomo Pharmaceuticals Company, Ltd. | Sustained-release preparation |
| US4797287A (en) * | 1984-06-19 | 1989-01-10 | Basf Aktiengesellschaft | Cylindrical microtablets |
| US4828843A (en) * | 1984-06-19 | 1989-05-09 | Basf Aktiengesellschaft | Cylindrical microtablets |
| US4849141A (en) * | 1985-12-27 | 1989-07-18 | Sumitomo Pharmaceuticals Company, Limited | Method for producing sustained release formulation |
| EP0268680A4 (en) * | 1986-05-29 | 1990-04-10 | Vnii Ispytatel Med Tech | Antitumor film of biodestructible polymers. |
| EP0268680A1 (en) * | 1986-05-29 | 1988-06-01 | Vsesojuzny Nauchno-Issledovatelsky I Ispytatelny Institut Meditsinskoi Tekhniki | Antitumor film of biodestructible polymers |
| EP0281482A1 (en) * | 1987-03-06 | 1988-09-07 | Research Triangle Institute | Polymer blends for selective biodegradability |
| US5183662A (en) * | 1990-08-30 | 1993-02-02 | Senju Pharmaceutical Co., Ltd. | Controlled drug release composition |
| US5567431A (en) * | 1991-03-14 | 1996-10-22 | Centre National De La Recherche Scientifique (Cnrs) | Polylactic acid-based implant susceptible of bioresorption containing and antibiotic |
| WO1992016193A1 (en) * | 1991-03-14 | 1992-10-01 | Centre National De La Recherche Scientifique (Cnrs) | Polylactic acid-based implant susceptible of bioresorption containing an antibiotic |
| FR2673843A1 (en) * | 1991-03-14 | 1992-09-18 | Centre Nat Rech Scient | IMPLANTABLE, BIORESORBABLE PHARMACEUTICAL COMPOSITION BASED ON POLY (LACTIC ACID), INTENDED TO IMPLEMENT A LOCAL INTERNAL ANTIBOTHERAPY. |
| US5545485A (en) * | 1993-09-14 | 1996-08-13 | Fujitsu Limited | Biodegradable resin molded article |
| US5542920A (en) * | 1994-09-12 | 1996-08-06 | Delab | Needle-less parenteral introduction device |
| WO1996008289A1 (en) * | 1994-09-12 | 1996-03-21 | Societe De Conseils De Recherches Et D'applications Scientifiques, S.A. | Needle-less parenteral introduction device |
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Also Published As
| Publication number | Publication date |
|---|---|
| GB2091554B (en) | 1984-09-12 |
| DE3200763C2 (en) | 1993-02-25 |
| CH650405A5 (en) | 1985-07-31 |
| DE3200763A1 (en) | 1982-11-25 |
| FR2497661B1 (en) | 1985-10-18 |
| FR2497661A1 (en) | 1982-07-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 732E | Amendments to the register in respect of changes of name or changes affecting rights (sect. 32/1977) | ||
| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 19990111 |