WO1995025545A1 - The use of dimeticone as a transport and carrier system and/or drug delivery system - Google Patents

The use of dimeticone as a transport and carrier system and/or drug delivery system Download PDF

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Publication number
WO1995025545A1
WO1995025545A1 PCT/EP1995/000973 EP9500973W WO9525545A1 WO 1995025545 A1 WO1995025545 A1 WO 1995025545A1 EP 9500973 W EP9500973 W EP 9500973W WO 9525545 A1 WO9525545 A1 WO 9525545A1
Authority
WO
WIPO (PCT)
Prior art keywords
pharmaceutical composition
combination
composition containing
dimeticone
dimethylpoly
Prior art date
Application number
PCT/EP1995/000973
Other languages
French (fr)
Inventor
Alfred Schmidt
Hans-Jürgen Upmeyer
Original Assignee
Alfred Schmidt
Upmeyer Hans Juergen
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Alfred Schmidt, Upmeyer Hans Juergen filed Critical Alfred Schmidt
Priority to CA002185883A priority Critical patent/CA2185883C/en
Priority to SK1324-96A priority patent/SK132496A3/en
Priority to US08/716,161 priority patent/US5834004A/en
Priority to NZ282805A priority patent/NZ282805A/en
Priority to AU20714/95A priority patent/AU706351B2/en
Priority to JP7524363A priority patent/JPH09510466A/en
Priority to CZ963007A priority patent/CZ300796A3/en
Priority to EP95913130A priority patent/EP0804242A1/en
Publication of WO1995025545A1 publication Critical patent/WO1995025545A1/en
Priority to NO963893A priority patent/NO963893L/en
Priority to FI963683A priority patent/FI963683A/en

Links

Classifications

    • 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
    • A61K31/80—Polymers containing hetero atoms not provided for in groups A61K31/755 - A61K31/795
    • 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
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/34—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyesters, polyamino acids, polysiloxanes, polyphosphazines, copolymers of polyalkylene glycol or poloxamers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents

Definitions

  • Dimeticone as a Transport and Carrier System and/or Drug Delivery System
  • the invention relates to dimethylpolysiloxane (dimeticone) to be used as a transport and carrier system and/or a drug delivery system for pharmaceutical drugs for instance for the treatment of gastro-intestinal diseases. Moreover, the invention relates to pharmaceutical compositions containing dimethylpolysiloxane as a transport and carrier system and/or as a drug delivery system in combination with an active ingredient and methods related thereto.
  • dimeticone-containing preparations are used to treat symptoms such as flatulence, sensation of repletion (bloating) and meteorism. Moreover, the use of dimeticone for treating inflammatory and ulcerous diseases of the esophagus, the stomach and the duodenum has been described.
  • the galenics of a pharmaceutical composition should be such that only the
  • the therapeutically active ingredient right at the site where it is to produce its effect or at the site where it is absorbed so as to increase the local bioavailability and/or general bioavailability of the active ingredient (for instance by averting a first pass effect in the liver) or so as to avoid systemic side effects as much as possible.
  • the continuous peristalsis, the variation of the chemical conditions over the length of the digestive tract, and the morphology of the surface of the GI tract are obstacles to a prolonged residence time in the different sections of the tract (such as the esophagus, stomach, duodenum, and colon) .
  • the present invention provides a carrier that lends itself for use in particular galenic pharmaceutical forms for oral, rectal and intraoperative applications which release and/or fix the active ingredient continuously at the very site where it is to produce its effect or is absorbed.
  • dimeticone because of its unique physico-chemical properties is ideally suited for such purposes.
  • Dimeticone has a very wide range of viscosities, depending on the degree of polymerization.
  • the viscosity of dimeticone to be used in accordance with the invention may vary, depending on the therapeutical purpose, the nature and location of the condition to be treated as well as the drug to be administered.
  • dimeticone having a kinematic viscosity in the range of 10 to 100,000 mm .S -1 is used.
  • dimeticone having a kinematic viscosity in the range of 300 to 1,500 mm .S "1 is particularly preferred. Dimeticone may also be supplemented with silicone dioxide as it is for example contained in the product Simeticone.
  • Dimeticone was found to show a particular association with or affinity to the surface structure of the GI tract. Because of an increased adhesion resulting from the adhesive properties of dimeticone, the residence time of an active ingredient in a region of the GI tract can be substantially prolonged if dimeticone is used as a transport or carrier system.
  • dimeticone because of the different chemical, morphological and physiological conditions along the GI tract, the affinity and association of dimeticone with the epithelial cells of the GI tract is not uniform. Thus, in order to optimize the effect of dimeticone as a transport and carrier system and/or drug delivery system for any particular drug at any particular site of the GI tract, dimeticone with the appropriate viscosity should be chosen, depending on the nature of the therapy and drug as well as the location in the GI tract. This may readily be determined' by experimentation.
  • dimeticone is not limited to the treatment of the GI tract. It may also be used in the treatment of the cardiovascular system the lungs, the brain and all hollow organs.
  • dimeticone was found to be particularly suitable as a transport and carrier system or a drug delivery system for cytostatic drugs, immunosup- pressants, immunomodulating and immunostimulative substances, biological response modifying (BRM) substances, radio-, chemo- and photosensitizers, anti-inflammatory substances, such as corticoids, antibiotics, analgesics, locally effective anestetics, antiphlogistics, non-steroidal antirheumatics, antiviral substances, bismuth preparations and motility inhibiting and motility enhancing substances.
  • BRM biological response modifying
  • dimeticone as a carrier for the photo- sensitizer ⁇ 5-amino levulinic acid (ALA) , the H-, antagonists (such as ranitidine and cimetidine) and the proton pump inhibitors (such as omeprazole and lansoprazole) is particularly preferred.
  • the pharmaceutical compositions which contain dimeticone in combination with one of the afore-mentioned substances therefore lend themselves particularly well for the treatment of inflammatory, infectious, ulcerous and neoplastic diseases of the GI tract.
  • the dimeticone-containing pharmaceutical composition may be formulated in an enteral form according to conventional methods in order to prevent dimeticone and the active ingredient from remaining in the upper zone of the GI tract.
  • the properties of the pharmaceutical composition should be so adjusted that it has an increased affinity for the lower part of the GI tract.
  • Direct application for instance via the bioptic channel of an endoscope, bronchoscope or proctoscope, intraoperative or by instillation, is particularly preferred.
  • the dimeticone-containing pharmaceutical composition should also contain highly dispersed silicon dioxide and/or a pharmaceutically acceptable surface-active agent.
  • the ratio of dimethylpolysiloxane to the surface-active agent is preferably 3 to 10 : 1, in particular 4 to 6 : 1, and the ratio of highly dispersed silicon dioxide to dimethylpolysiloxane is preferably 3 to 50% (wt/wt) .
  • a preferred range for the latter ratio is 30 to 40% (wt/wt) , the value of 35 to 36% being particularly preferred.
  • the concentration of the surface active agent is preferably at least 1.5 % (wt/wt).
  • a particularly preferred dimeticone formulation contains 8-10% (wt/wt) of the surface active agent.
  • Stearic salts or long chain alkanoic acids in particular C- j ⁇ -C- ⁇ g alkanoic acids, such as myristic acid, palmitic acid and stearic acid, and their salts, such as magnesium or calcium salts and mixtures thereof can be suitably used as pharmaceutically acceptable surface active agents.
  • ALA ⁇ -amino levulinic acid containing emulsion
  • colloidal magnesium aluminum silicate
  • the emulsion of the Example is intended for the photodynamic therapy of tumors of the GI tract, the emulsion being applied by means of an endoscope at the very site where the effect is to be elicited.

Abstract

The invention relates to dimethylpolysiloxane (dimeticone) to be used as a transport and carrier system and/or a drug delivery system for pharmaceutical drugs. Moreover, the invention relates to pharmaceutical compositions containing dimethylpolysiloxane as a transport and carrier system and/or as a drug delivery system in conbination with an active ingredient.

Description

The Use of Dimeticone as a Transport and Carrier System and/or Drug Delivery System
TECHNICAL FIELD OF THE INVENTION
The invention relates to dimethylpolysiloxane (dimeticone) to be used as a transport and carrier system and/or a drug delivery system for pharmaceutical drugs for instance for the treatment of gastro-intestinal diseases. Moreover, the invention relates to pharmaceutical compositions containing dimethylpolysiloxane as a transport and carrier system and/or as a drug delivery system in combination with an active ingredient and methods related thereto.
Commercial dimeticone-containing preparations are used to treat symptoms such as flatulence, sensation of repletion (bloating) and meteorism. Moreover, the use of dimeticone for treating inflammatory and ulcerous diseases of the esophagus, the stomach and the duodenum has been described.
BACKGROUND OF THE INVENTION
In order to avoid dose-related side effects, the galenics of a pharmaceutical composition should be such that only the
dose of the active ingredient necessary to elicit the desired therapeutic effect needs to be administered.
Hence, it is desirable to apply the therapeutically active ingredient right at the site where it is to produce its effect or at the site where it is absorbed so as to increase the local bioavailability and/or general bioavailability of the active ingredient (for instance by averting a first pass effect in the liver) or so as to avoid systemic side effects as much as possible.
In view of the different physiological properties of the different sections of the gastro-intestinal tract (GI tract) , local therapy is particularly difficult in this case.
The continuous peristalsis, the variation of the chemical conditions over the length of the digestive tract, and the morphology of the surface of the GI tract are obstacles to a prolonged residence time in the different sections of the tract (such as the esophagus, stomach, duodenum, and colon) .
Especially in the case of chronic diseases, such as inflammatory, infectious, ulcerous or neoplastic changes of the GI tract, direct local therapy capable of being continued over a prolonged period of time is desirable.
Furthermore, local treatment is also desirable in the case of disorders in the cardiovascular system, the lungs, the brain, and all hollow organs.
Local treatment requires a suitable transport and carrier system and/or drug delivery system. SUMMARY OF THE INVENTION
The present invention provides a carrier that lends itself for use in particular galenic pharmaceutical forms for oral, rectal and intraoperative applications which release and/or fix the active ingredient continuously at the very site where it is to produce its effect or is absorbed.
It was surprisingly found that dimeticone, because of its unique physico-chemical properties is ideally suited for such purposes. Dimeticone has a very wide range of viscosities, depending on the degree of polymerization. The viscosity of dimeticone to be used in accordance with the invention may vary, depending on the therapeutical purpose, the nature and location of the condition to be treated as well as the drug to be administered. Preferably, dimeticone having a kinematic viscosity in the range of 10 to 100,000 mm .S-1 is used.
The use of dimeticone having a kinematic viscosity in the range of 300 to 1,500 mm .S"1 is particularly preferred. Dimeticone may also be supplemented with silicone dioxide as it is for example contained in the product Simeticone.
Dimeticone was found to show a particular association with or affinity to the surface structure of the GI tract. Because of an increased adhesion resulting from the adhesive properties of dimeticone, the residence time of an active ingredient in a region of the GI tract can be substantially prolonged if dimeticone is used as a transport or carrier system.
However, because of the different chemical, morphological and physiological conditions along the GI tract, the affinity and association of dimeticone with the epithelial cells of the GI tract is not uniform. Thus, in order to optimize the effect of dimeticone as a transport and carrier system and/or drug delivery system for any particular drug at any particular site of the GI tract, dimeticone with the appropriate viscosity should be chosen, depending on the nature of the therapy and drug as well as the location in the GI tract. This may readily be determined' by experimentation.
The use of dimeticone is not limited to the treatment of the GI tract. It may also be used in the treatment of the cardiovascular system the lungs, the brain and all hollow organs.
According to the invention, dimeticone was found to be particularly suitable as a transport and carrier system or a drug delivery system for cytostatic drugs, immunosup- pressants, immunomodulating and immunostimulative substances, biological response modifying (BRM) substances, radio-, chemo- and photosensitizers, anti-inflammatory substances, such as corticoids, antibiotics, analgesics, locally effective anestetics, antiphlogistics, non-steroidal antirheumatics, antiviral substances, bismuth preparations and motility inhibiting and motility enhancing substances.
The function of dimeticone as a carrier for the photo- sensitizer <5-amino levulinic acid (ALA) , the H-, antagonists (such as ranitidine and cimetidine) and the proton pump inhibitors (such as omeprazole and lansoprazole) is particularly preferred.
The pharmaceutical compositions which contain dimeticone in combination with one of the afore-mentioned substances therefore lend themselves particularly well for the treatment of inflammatory, infectious, ulcerous and neoplastic diseases of the GI tract. In the treatment of disorders in the lower area of the GI tract, the dimeticone-containing pharmaceutical composition may be formulated in an enteral form according to conventional methods in order to prevent dimeticone and the active ingredient from remaining in the upper zone of the GI tract. Alternatively, the properties of the pharmaceutical composition should be so adjusted that it has an increased affinity for the lower part of the GI tract.
Direct application, for instance via the bioptic channel of an endoscope, bronchoscope or proctoscope, intraoperative or by instillation, is particularly preferred.
The dimeticone-containing pharmaceutical composition should also contain highly dispersed silicon dioxide and/or a pharmaceutically acceptable surface-active agent.
The ratio of dimethylpolysiloxane to the surface-active agent is preferably 3 to 10 : 1, in particular 4 to 6 : 1, and the ratio of highly dispersed silicon dioxide to dimethylpolysiloxane is preferably 3 to 50% (wt/wt) . A preferred range for the latter ratio is 30 to 40% (wt/wt) , the value of 35 to 36% being particularly preferred.
The concentration of the surface active agent is preferably at least 1.5 % (wt/wt). A particularly preferred dimeticone formulation contains 8-10% (wt/wt) of the surface active agent.
Stearic salts or long chain alkanoic acids, in particular C-j^-C-^g alkanoic acids, such as myristic acid, palmitic acid and stearic acid, and their salts, such as magnesium or calcium salts and mixtures thereof can be suitably used as pharmaceutically acceptable surface active agents.
The invention is illustrated by the following example. Example
δ-amino levulinic acid containing emulsion (ALA)
amount/dose g / 250 ml
ALA 5,000.0000 simeticone
(dimeticone 1000 - Si02 94:6) 2,000.0000
Aerosil 200 125.0000
Kollidon CL M1 2,500.0000 hydroxyethylcellulose 20,000.0000
Veegum K2 2,500.0000 cinnamon oil DA B 10 0.1228
85% indigotin 0.0250 water, purified ad 250 ml
1 = polyvinylpyrrolidone (INN: providone)
2 = colloidal magnesium = aluminum silicate
The emulsion of the Example is intended for the photodynamic therapy of tumors of the GI tract, the emulsion being applied by means of an endoscope at the very site where the effect is to be elicited.
While we have described an embodiment of this invention, it is apparent that our embodiment may be altered to provide other embodiments which utilize the method of this invention. Therefore, it will be appreciated that the scope of this invention is to be defined by the appended claims, rather than by the specific embodiment which has been presented by way of example.

Claims

We Claim:
1. The use of dimethylpolysiloxane as a transport or carrier system for active ingredients for the preparation of a pharmaceutical composition.
2. A pharmaceutical composition containing dimethyl¬ polysiloxane in combination with a photosensitizer.
3. The pharmaceutical composition according to claim 2 wherein the photosensitizer is <S-amino levulinic acid ALA.
4. A pharmaceutical composition containing dimethyl¬ polysiloxane in combination with an H2-antagonist and/or a proton pump inhibitor.
5. A pharmaceutical composition containing dimethyl¬ polysiloxane in combination with one or more anti¬ biotics.
6. A pharmaceutical composition containing dimethyl¬ polysiloxane in combination with an immunomodulating substance or an immunostimulating substance.
7. A pharmaceutical composition containing dimethylpoly¬ siloxane in combination with an analgesic or locally effective anesthetic.
8. A pharmaceutical composition containing dimethylpoly¬ siloxane in combination with an antiphlogistic or non- steroidal antirheumatic.
9. A pharmaceutical composition containing dimethylpoly¬ siloxane in combination with an anti-viral substance.
10. The use according to claim 1, wherein the active ingredient is a corticoid.
11. A pharmaceutical composition containing dimethylpoly¬ siloxane in combination with a bismuth preparation.
12. A pharmaceutical composition containing dimethylpoly¬ siloxane in combination with a motility-inhibiting or motility-enhancing substance.
13. A pharmaceutical composition containing dimethylpoly¬ siloxane in combination with BRM (biological response modifying) substances.
PCT/EP1995/000973 1994-03-18 1995-03-15 The use of dimeticone as a transport and carrier system and/or drug delivery system WO1995025545A1 (en)

Priority Applications (10)

Application Number Priority Date Filing Date Title
CA002185883A CA2185883C (en) 1994-03-18 1995-03-15 The use of dimeticone as a transport and carrier system and/or drug delivery system
SK1324-96A SK132496A3 (en) 1994-03-18 1995-03-15 The use of dimeticone as a transport and carrier system and/or drug delivery system
US08/716,161 US5834004A (en) 1994-03-18 1995-03-15 Enteral composition comprising dimethicone and a photosensitizer and a method of delivery
NZ282805A NZ282805A (en) 1994-03-18 1995-03-15 Use of dimethylpolysiloxane (dimeticone) as a carrier in medicaments
AU20714/95A AU706351B2 (en) 1994-03-18 1995-03-15 The use of dimeticone as a transport and carrier system and/or drug delivery system
JP7524363A JPH09510466A (en) 1994-03-18 1995-03-15 Use of dimethicone as transportation and carrier system and / or drug delivery system
CZ963007A CZ300796A3 (en) 1994-03-18 1995-03-15 Use of dimeticon as transpot and supporting system and/or a medicament delivering system
EP95913130A EP0804242A1 (en) 1994-03-18 1995-03-15 The use of dimeticone as a transport and carrier system and/or drug delivery system
NO963893A NO963893L (en) 1994-03-18 1996-09-17 Use of dimeticone as a transport and carrier system and / or drug delivery system
FI963683A FI963683A (en) 1994-03-18 1996-09-17 Use of dimethicone as a transport and carrier system and / or drug delivery system

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE4409357A DE4409357C2 (en) 1994-03-18 1994-03-18 Use of Dimeticon to eradicate Heliobacter pylori
DEP4409357.8 1994-03-18

Publications (1)

Publication Number Publication Date
WO1995025545A1 true WO1995025545A1 (en) 1995-09-28

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1995/000973 WO1995025545A1 (en) 1994-03-18 1995-03-15 The use of dimeticone as a transport and carrier system and/or drug delivery system

Country Status (14)

Country Link
EP (1) EP0804242A1 (en)
JP (1) JPH09510466A (en)
CN (1) CN1244129A (en)
AU (1) AU699199B2 (en)
CA (1) CA2185882A1 (en)
CZ (1) CZ300796A3 (en)
DE (1) DE4409357C2 (en)
FI (1) FI963682A (en)
HU (1) HU215595B (en)
NO (1) NO963893L (en)
NZ (1) NZ282805A (en)
PL (1) PL316307A1 (en)
SK (1) SK132496A3 (en)
WO (1) WO1995025545A1 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6100245A (en) * 1999-09-07 2000-08-08 Mcneil-Ppc, Inc. Use of simethicone to treat ulcerative colitis

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004103343A1 (en) * 2003-05-25 2004-12-02 Yuwan Wang Dimeticone-containing sustained formulation

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR3848M (en) * 1964-05-04 1966-01-17 Robert Schapiro Therapeutic associations for the treatment of numerous organic or functional digestive disorders.
FR2110314A1 (en) * 1970-10-09 1972-06-02 Angeli Inst Spa
EP0219076A2 (en) * 1985-10-11 1987-04-22 Sumitomo Pharmaceuticals Company, Limited Sustained release composition
US4837029A (en) * 1987-04-06 1989-06-06 Carolina Medical Products, Inc. Low foaming, aqueously homogenizable rifampin composition
WO1991004034A1 (en) * 1989-09-15 1991-04-04 Pehrom Pharmaceutical Corporation Topical preparation for treatment of aphthous ulcers and other lesions
EP0428296A2 (en) * 1989-11-01 1991-05-22 McNEIL-PPC, INC. Pharmaceutical compositions for treating gastrointestinal distress
US5229137A (en) * 1992-05-06 1993-07-20 Brigham And Women's Hospital, Inc. Methods and pharmaceutical compositions for treating episodic heartburn
WO1994003209A1 (en) * 1992-07-29 1994-02-17 Merck & Co., Inc. Dexibuprofen/antacid/simethicone combinations
WO1995005813A1 (en) * 1993-08-27 1995-03-02 Noven Pharmaceuticals, Inc. COMPOSITIONS AND METHODS FOR THE ADMINISTRATION OF δ-AMINOLEVULINIC ACID

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU637570B2 (en) * 1989-01-19 1993-06-03 Alfred Schmidt Use of dimethylpolysiloxane for treating disorders of the gastrointestinal tract

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR3848M (en) * 1964-05-04 1966-01-17 Robert Schapiro Therapeutic associations for the treatment of numerous organic or functional digestive disorders.
FR2110314A1 (en) * 1970-10-09 1972-06-02 Angeli Inst Spa
EP0219076A2 (en) * 1985-10-11 1987-04-22 Sumitomo Pharmaceuticals Company, Limited Sustained release composition
US4837029A (en) * 1987-04-06 1989-06-06 Carolina Medical Products, Inc. Low foaming, aqueously homogenizable rifampin composition
WO1991004034A1 (en) * 1989-09-15 1991-04-04 Pehrom Pharmaceutical Corporation Topical preparation for treatment of aphthous ulcers and other lesions
EP0428296A2 (en) * 1989-11-01 1991-05-22 McNEIL-PPC, INC. Pharmaceutical compositions for treating gastrointestinal distress
US5229137A (en) * 1992-05-06 1993-07-20 Brigham And Women's Hospital, Inc. Methods and pharmaceutical compositions for treating episodic heartburn
WO1994003209A1 (en) * 1992-07-29 1994-02-17 Merck & Co., Inc. Dexibuprofen/antacid/simethicone combinations
WO1995005813A1 (en) * 1993-08-27 1995-03-02 Noven Pharmaceuticals, Inc. COMPOSITIONS AND METHODS FOR THE ADMINISTRATION OF δ-AMINOLEVULINIC ACID

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6100245A (en) * 1999-09-07 2000-08-08 Mcneil-Ppc, Inc. Use of simethicone to treat ulcerative colitis
EP1084706A2 (en) * 1999-09-07 2001-03-21 McNEIL-PPC, INC. Use of simethicone to treat ulcerative colitis
EP1084706A3 (en) * 1999-09-07 2002-07-17 McNEIL-PPC, INC. Use of simethicone to treat ulcerative colitis

Also Published As

Publication number Publication date
JPH09510466A (en) 1997-10-21
AU699199B2 (en) 1998-11-26
HUT75711A (en) 1997-05-28
FI963682A0 (en) 1996-09-17
NO963893L (en) 1996-11-04
AU2071395A (en) 1995-10-09
HU9602839D0 (en) 1996-12-30
FI963682A (en) 1996-11-13
PL316307A1 (en) 1997-01-06
DE4409357A1 (en) 1995-09-21
CN1244129A (en) 2000-02-09
CZ300796A3 (en) 1997-09-17
CA2185882A1 (en) 1995-09-28
DE4409357C2 (en) 1996-10-17
HU215595B (en) 1999-01-28
SK132496A3 (en) 1997-06-04
NO963893D0 (en) 1996-09-17
NZ282805A (en) 1998-02-26
EP0804242A1 (en) 1997-11-05

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