WO1998003162A1 - Compositions medicinales - Google Patents

Compositions medicinales Download PDF

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Publication number
WO1998003162A1
WO1998003162A1 PCT/JP1997/002448 JP9702448W WO9803162A1 WO 1998003162 A1 WO1998003162 A1 WO 1998003162A1 JP 9702448 W JP9702448 W JP 9702448W WO 9803162 A1 WO9803162 A1 WO 9803162A1
Authority
WO
WIPO (PCT)
Prior art keywords
pharmaceutical composition
cyclodextrin
composition according
weight
pharmaceutically acceptable
Prior art date
Application number
PCT/JP1997/002448
Other languages
English (en)
Japanese (ja)
Inventor
Atsushi Sakai
Rumiko Kuma
Tsuneo Fujii
Tadashi Mishina
Kenji Chiba
Original Assignee
Yoshitomi Pharmaceutical Industries, Ltd.
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 Yoshitomi Pharmaceutical Industries, Ltd. filed Critical Yoshitomi Pharmaceutical Industries, Ltd.
Priority to AU34608/97A priority Critical patent/AU3460897A/en
Publication of WO1998003162A1 publication Critical patent/WO1998003162A1/fr
Priority to US09/231,484 priority patent/US6476004B1/en

Links

Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y5/00—Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery
    • 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
    • A61K31/13—Amines
    • A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
    • 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
    • A61K47/69—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 conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit
    • A61K47/6949—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 conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes
    • A61K47/6951—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 conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes using cyclodextrin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders

Definitions

  • the present invention relates to a pharmaceutical composition containing 2-amino-2- [2- (4-octylphenyl) ethyl] propane-1,3-diol or a pharmaceutically acceptable acid addition salt thereof as an active ingredient. More specifically, 2-amino-2 2- [2- ( 4-year-old octylphenyl) ethyl] propane-1,3-diol or a pharmaceutically acceptable acid addition salt thereof with a cyclodextrin compound, and a pharmaceutical composition which can be formulated as a liquid preparation. .
  • the present inventors have proposed a method for preparing 2-amino-2- [2-1 (41 years old) which can be used as a liquid preparation such as an injection or an ophthalmic solution with little side effects such as hemolysis and little local irritation.
  • [Cutylphenyl] ethyl] Propane-1,3-diol or a pharmaceutically acceptable acid addition salt thereof was obtained through a variety of studies to obtain a pharmaceutical composition.
  • the present invention has been completed.
  • the present invention is characterized in that cyclodextrins are blended with 2-amino-2- [2- (4-year-old octylphenyl) ethyl] propane-1,3-diol or a pharmaceutically acceptable acid addition salt thereof. It is intended to provide a pharmaceutical composition which is easy to formulate, has reduced side effects such as hemolysis, and is suitable for a liquid preparation having little local irritation.
  • the present invention has also found that, by further adding a saccharide selected from a monosaccharide, a disaccharide and a sugar alcohol to the composition, a liquid composition having further improved irritation can be obtained.
  • the pharmaceutical composition of the present invention comprises 2-amino-2- [2- (4-octylphenyl) ethyl] propane-1,3-diol or a pharmaceutically acceptable acid addition salt thereof, a cyclodextrin, if desired, as an active ingredient. And a saccharide, and a conventional pharmaceutically acceptable carrier or diluent, preferably a carrier or diluent suitable for liquids.
  • 2-amino-2- [2- (4 One year old octylphenyl) ethyl] propane-1,3-diol or a pharmaceutically acceptable acid addition salt thereof can be produced by the method described in International Publication W094 / 08943.
  • a preferred compound is 2-amino-2- [21- (4-year-old tylphenyl) ethyl] propane-1,3-diol hydrochloride.
  • 2-amino-2- [2- (4-year-old octylphenyl) ethyl] propane-1,3-diol or a pharmaceutically acceptable acid addition salt thereof is added in an amount of 0.01% based on the total weight of the composition. -20% by weight, especially 0.1-10% by weight is preferred.
  • the cyclodextrin used in the present invention is a natural cyclodextrin, a branched cyclodextrin, an alkylene cyclodextrin or a hydroxyalkylcyclodextrin, and specifically, -cyclodextrin.
  • the saccharide used in the present invention is selected from monosaccharides, disaccharides and sugar alcohols, and specifically, glucose, fructose, D-maltose, lactose, sucrose (sucrose), D-mannitol, D-xylitol , D-sorbitol, and these can be used alone or in combination of two or more.
  • the amount of these saccharides is from 1 to 3 parts by weight per part by weight of 2-amino-2-12- (4-year-old octylphenyl) ethyl] propane-1,3-diol or a pharmaceutically acceptable acid addition salt thereof. 100 parts by weight, especially 5 to 80 parts by weight, is preferred.
  • the pharmaceutical form of the pharmaceutical composition of the present invention is a liquid, specifically, an injection, an eye drop, a nasal drop, an ear drop, a drop, a liquid for oral administration, a liquid for inhalation, and a mouth lotion.
  • the pharmaceutical composition of the present invention can be commercially available as a finished liquid preparation, or can be commercially available as a kit of a powder or a lyophilized product containing an active ingredient or the like and a lyophilized solution.
  • the active ingredient 2-amino-2- [2- (4-octylphenyl) ethyl] propane-1.3-diol or its pharmaceutically acceptable acid addition salt (particularly hydrochloride) is dissolved in purified water. After aseptic filtration, the obtained solution is filled in a vial, and then freeze-dried under vacuum to obtain a freeze-dried product.
  • an aqueous solution in which the cyclodextrins used in the present invention and, if necessary, saccharides are dissolved in distilled water is prepared.
  • the freeze-dried product may be dissolved in the dissolution solution before use.
  • These lysates are 2-amino-21- (2- (4-year-old octylphenyl) ethyl) propane-1, 3-diol
  • the pharmaceutically acceptable acid addition salt is used in a 5-fold to 2000-fold amount (weight part) with respect to the pharmaceutically acceptable acid addition salt.
  • distilled water is preferably distilled water for injection.
  • the freeze-dried product is usually filled in a vial, replaced with nitrogen, sealed with a rubber stopper, and sealed with aluminum, so that it can be stored at room temperature for a long period of time.
  • the cyclodextrins and the saccharides to be added as required are not added to the dissolution solution as described above, but instead of the active ingredient 2-amino-2- [2- (4-octylphenyl) ethyl] propane
  • the lyophilized product may be contained together with 1,3-diol or a pharmaceutically acceptable acid addition salt thereof.
  • the amount of cyclodextrin is preferably 1 to 50 parts by weight, particularly preferably 10 to 30 parts by weight, based on 1 part by weight of the active ingredient.
  • the saccharides to be added as required are preferably 1 to 100 parts by weight, particularly preferably 5 to 80 parts by weight, per 1 part by weight of the active ingredient.
  • a solvent for example, a solvent, a tonicity agent, a pH adjuster, a buffer, an antioxidant, a thickener, a surfactant, a preservative, a humectant,
  • a flavoring agent, a coloring agent, and the like can also be appropriately compounded.
  • these additives can be added when formulating the composition of the present invention, and are dissolved when used in the above kit preparation. Can also be added to the dissolving solution.
  • the pharmaceutical composition of the present invention can be used as a liquid preparation, particularly as a method for suppressing rejection after organ or bone marrow transplantation, maintaining immunotherapy, eye diseases such as Behcet's disease or uveitis, psoriasis, atopic dermatitis, and contact. It can be used for the treatment of dermatitis including dermatitis and allergic dermatitis. More specifically, the pharmaceutical preparation of the present invention is useful for the prevention or treatment of various indications (immunosuppression in organ or bone marrow transplantation, various autoimmune diseases, various allergic diseases, etc.) conventionally performed with oral preparations. Can be used.
  • composition of the present invention can be used as a liquid preparation for organ or tissue transplantation.
  • ⁇ Torted paper For example, resistance to heart, kidney, liver, lung, bone marrow, cornea, fallen, small intestine, limb, muscle, nerve, fat marrow, duodenum, skin *, transplantation of islet cells, xenograft) Or rejection, graft-versus-host (GvH) disease due to bone marrow or small bowel transplantation, autoimmune diseases such as rheumatoid arthritis, systemic lupus erythematosus, nephrotic syndrome lupus, Hashimoto goiter, multiple sclerosis , Myasthenia gravis, type I diabetes, type II diabetes mellitus, uveitis, nephrotic syndrome, steroid-dependent and steroid-resistant nephrosis, palmar plantar pustulosis, allergic encephalomyelitis, glomerulonephritis Etc., and for the treatment and prevention of infectious diseases caused by pathogenic microorganisms
  • the onset of inflammatory, proliferative and hyperproliferative skin diseases, and immune-mediated diseases in the skin such as psoriasis, psoriatic arthritis, topical eczema (atopic dermatitis), contact dermatitis, and (Eczema dermatitis, seborrheic skin) * flame, lichen planus, pemphigus, bullous pemphigoid, epidermolysis bullosa, urticaria, vascular edema, vasculitis, erythema, increased skin eosinophils It can also be used to treat acne, acne, alopecia areata, eosinophilic fasciitis and atherosclerosis.
  • the compositions of the invention more particularly prevent alopecia, form hair buds and / or develop and grow hair, so that female or male pattern baldness or senile alopecia It can be used to do hair restoration, such as treatment for hair.
  • compositions of the invention may be used for respiratory diseases such as sarcoidosis, pulmonary fibrosis, idiopathic interstitial pneumonia and reversible obstructive airway diseases such as bronchial asthma, pediatric asthma, allergic asthma, intrinsic asthma, extrinsic asthma It is also applicable to the treatment of asthma, including dusty asthma, especially chronic or refractory asthma (eg, late onset asthma and airway hyperreactivity), bronchitis and the like.
  • the composition of the present invention can also be used for treating liver damage associated with ischemia.
  • eye diseases such as conjunctivitis, keratoconjunctivitis, keratitis, spring catarrhals and Behcet's disease It is also effective for severe uveitis, herpes keratitis, keratoconus, corneal epithelial degeneration, corneal vitiligo, pemphigus, Mohren's ulcer, scleritis, Graves' eye disease and severe intraocular inflammation.
  • eye diseases such as conjunctivitis, keratoconjunctivitis, keratitis, spring catarrhals and Behcet's disease It is also effective for severe uveitis, herpes keratitis, keratoconus, corneal epithelial degeneration, corneal vitiligo, pemphigus, Mohren's ulcer, scleritis, Graves' eye disease and severe intraocular inflammation.
  • composition of the present invention also includes mucosal or vascular inflammation [eg, leukotriene B4-mediated disease, stomach ulcer, vascular injury due to ischemic disease and thrombotic disease, ischemic bowel disease, inflammatory bowel disease (eg, Crohn's disease and ulcerative colitis), necrotizing colitis], and can also be used to prevent or treat intestinal damage associated with burns.
  • mucosal or vascular inflammation eg, leukotriene B4-mediated disease, stomach ulcer, vascular injury due to ischemic disease and thrombotic disease, ischemic bowel disease, inflammatory bowel disease (eg, Crohn's disease and ulcerative colitis), necrotizing colitis
  • the composition of the present invention is selected from gastric diseases such as interstitial nephritis, Good Bastian syndrome, hemolytic uremic syndrome and diabetic nephropathy; polymyositis, Guillain-Barre syndrome, Meniere's disease and radiculopathy Endocrine disorders such as hyperthyroidism and Graves' disease; pure erythrocytosis, aplastic anemia, aplastic anemia, idiopathic thrombocytopenic purpura, autoimmune hemolytic anemia, granules Blood diseases such as cytopenia and lack of erythropoiesis: bone diseases such as osteoporosis; respiratory diseases such as sarcoidosis, pulmonary fibrosis and idiopathic interstitial pneumonia: skin myositis, vulgaris Dermatosis such as vitiligo, fish vulgaris, psoriasis, photoallergic susceptibility and percutaneous T-cell lymphoma; cardiovascular diseases such as arteriosclerosis, a
  • compositions of the present invention may be used to treat intestinal inflammation Z allergies, such as Coe iac disease, proctitis, eosinophilic gastroenteritis, mastocytosis, Crohn's disease, and ulcerative colitis; and food-related allergic diseases It is suitable for the prevention or treatment of symptoms that are not directly related to the gastrointestinal tract, such as migraine, soreness and eczema.
  • the composition of the present invention since the composition of the present invention has an activity of promoting hypertrophy and hyperplasia of hepatic cells, the composition of the present invention includes immunogenic diseases (eg, including autoimmune hepatitis, primary biliary cirrhosis, and sclerosing cholangitis).
  • Immungenic diseases eg, including autoimmune hepatitis, primary biliary cirrhosis, and sclerosing cholangitis.
  • Chronic autoimmune liver disease eg, partial liver resection, acute liver death (eg, toxin, viral hepatitis, soil death due to shock or oxygen deprivation), viral hepatitis B, non-A / non-B hepatitis
  • acute liver death eg, toxin, viral hepatitis, soil death due to shock or oxygen deprivation
  • viral hepatitis B non-A / non-B hepatitis
  • composition of the present invention can also be used as a composition for an antibacterial agent, and thus can be used for treating diseases caused by pathogenic microorganisms and the like.
  • the composition of the present invention may be used for the treatment of malignant rheumatoid arthritis, amyloidosis, fulminant hepatitis, Shy 'Dore-Iger syndrome, pustular psoriasis, Behcet's disease, systemic lupus erythematosus, endocrine ophthalmopathy, progressive systemic sclerosis, mixed sexual connective tissue disease, aortic inflammation group, Wegener's granuloma, active chronic hepatitis, Evans syndrome, hay fever, idiopathic hypoparathyroidism, Addison's disease (autoimmune adrenalitis), autoimmune orchitis , Autoimmune ovitis, cold hemagglutininosis, paroxysmal cold hemoglobinuria, pernicious anemia, adult
  • composition of the present invention can be optionally used in combination with other immunosuppressants, steroid agents (blednisolone, methylprednisolone, dexamethasone, hydrocortisone, etc.) or non-steroid anti-inflammatory agents.
  • steroid agents blednisolone, methylprednisolone, dexamethasone, hydrocortisone, etc.
  • non-steroid anti-inflammatory agents are particularly preferred as other immunosuppressants.
  • immunosuppressants are azathioprine, brequinar sodium, deoxyspargarine, mizoribine, mycophenolic acid 2 One selected from monomorpholinethyl ester, cyclosporine, rapamycin, tacrolimus hydrate, leflunomide and OKT-3.
  • composition of the present invention may vary depending on the indication, its symptoms, the gender and age of the patient, the place of application, and the like.
  • the present compound is preferably used in an amount of 0.001 to 20% by weight, preferably 0.0000.
  • 1 to 10% by weight once or several times a day for example, 2 to 5 times
  • a clinically favorable effect can be obtained.
  • the present compound means 2-amino-2- [2- (4-year-old butylyl) ethyl] propane-11,3-diol hydrochloride.
  • D-mannitol 5.0% The above composition is dissolved in distilled water for injection to give a total injection of 10 ml. C If necessary, ordinary additives such as a preservative may be blended.
  • the above composition is dissolved in distilled water for injection (can be mixed with usual additives such as preservatives, if necessary). After aseptic filtration, a total of 1 Om1 is filled in a vial and freeze-dried according to a conventional method. And use it as an injection.
  • the above composition is dissolved in distilled water for injection (where necessary, conventional additives such as preservatives may be added). After aseptic filtration, a total of 1 Om1 is filled into a vial, and frozen according to a conventional method. Dry and use as injection.
  • Example 6 The above composition is dissolved in distilled water for injection to give a total of 1 Oml of injection. C If necessary, ordinary additives such as a preservative may be blended. Example 6
  • This compound 0.1% ⁇ -cyclodextrin (trade name: Celdex A-100) 1.0% D-mannitol 5.0 ⁇
  • the above composition is dissolved in sterile purified water, and the total amount of eye drops is 10m ⁇ . And If necessary, ordinary additives such as a preservative may be added.
  • D-mannitol 5.0% The above composition is dissolved in sterile purified water to give a total amount of 1% ophthalmic solution. If necessary, ordinary additives such as a preservative may be added.
  • Example 1 The formulation of Example 1 was repeatedly administered intravenously to a 5-week-old LEW rat for 5 days, and the swelling ratio of the tail ⁇ (tail diameter of the drug-administered group-diameter of the control tail) ⁇ tail of the control Confirm the presence or absence of local irritation using the diameter x 100 ⁇ as an index As a result, the result was 0% in Example 1, indicating that the preparation of Example 1 did not show local irritation.
  • Pharmaceutical compositions suitable for solutions containing diol or a pharmaceutically acceptable acid addition salt thereof are provided.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nanotechnology (AREA)
  • Epidemiology (AREA)
  • Biophysics (AREA)
  • Ophthalmology & Optometry (AREA)
  • Biotechnology (AREA)
  • General Engineering & Computer Science (AREA)
  • Medical Informatics (AREA)
  • Molecular Biology (AREA)
  • Crystallography & Structural Chemistry (AREA)
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  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

Compositions médicinales pouvant être traitées sous forme de solutions et destinées à être utilisées pour inhiber les réactions de rejet dans le cadre de la transplantation d'organes ou de moelle osseuse, dans l'immunothérapie d'entretien à cet effet ou pour le traitement de maladies auto-immunes, caractérisées en ce qu'elles contiennent du 2-amino-2-[2-(4-octylphényl)éthyl]propane-1,3-diol ou leurs sels d'addition d'acide pharmaceutiquement acceptables et des cyclodextrines, éventuellement, le cas échéant, avec des saccharides.
PCT/JP1997/002448 1996-07-18 1997-07-15 Compositions medicinales WO1998003162A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
AU34608/97A AU3460897A (en) 1996-07-18 1997-07-15 Medicinal compositions
US09/231,484 US6476004B1 (en) 1996-07-18 1999-01-14 Pharmaceutical composition

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP18938096A JP2002241272A (ja) 1996-07-18 1996-07-18 医薬処方組成物
JP8/189380 1996-07-18

Related Child Applications (1)

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US09/231,484 Continuation-In-Part US6476004B1 (en) 1996-07-18 1999-01-14 Pharmaceutical composition

Publications (1)

Publication Number Publication Date
WO1998003162A1 true WO1998003162A1 (fr) 1998-01-29

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Application Number Title Priority Date Filing Date
PCT/JP1997/002448 WO1998003162A1 (fr) 1996-07-18 1997-07-15 Compositions medicinales

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JP (1) JP2002241272A (fr)
AU (1) AU3460897A (fr)
WO (1) WO1998003162A1 (fr)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998037875A1 (fr) * 1997-02-27 1998-09-03 Yoshitomi Pharmaceutical Industries, Ltd. Composition medicamenteuse
WO1999036065A1 (fr) * 1998-01-19 1999-07-22 Yoshitomi Pharmaceutical Industries, Ltd. Compositions medicinales
WO2001001978A1 (fr) * 1999-06-30 2001-01-11 Mitsubishi Pharma Corporation Compositions de medicaments servant a prevenir ou a traiter la myocardite virale
US6423739B1 (en) 2000-02-23 2002-07-23 Daiichi Pharmaceutical Co., Ltd. Method for aiding cerebral recovery following neurodegeneration
US6437165B1 (en) 2000-08-31 2002-08-20 Merck & Co., Inc. Phosphate derivatives as immunoregulatory agents
EP1312359A2 (fr) * 1996-11-19 2003-05-21 Novartis AG Utilisation de derives de 1,3-propanediol
US8324283B2 (en) 2003-04-08 2012-12-04 Novartis Ag Solid pharmaceutical compositions comprising a SIP receptor agonist and a sugar alcohol

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2002324026B2 (en) * 1996-07-18 2005-07-14 Novartis Ag Pharmaceutical compositions
JP4838497B2 (ja) * 2004-04-09 2011-12-14 キッセイ薬品工業株式会社 肝移植後の拒絶反応の予防または治療用医薬組成物

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS58148816A (ja) * 1982-02-27 1983-09-05 Nippon Zenyaku Kogyo Kk 低刺激性チアムリン注射剤
JPH05213757A (ja) * 1990-08-13 1993-08-24 Senju Pharmaceut Co Ltd 水性液剤
JPH0616547A (ja) * 1992-07-01 1994-01-25 Wakamoto Pharmaceut Co Ltd 消炎点眼剤
WO1994008943A1 (fr) * 1992-10-21 1994-04-28 Yoshitomi Pharmaceutical Industries, Ltd. Compose 2-amino-1,3-propanediol et immunosuppresseur
JPH07228532A (ja) * 1993-04-22 1995-08-29 Senju Pharmaceut Co Ltd 水性液剤、その有効成分の溶解性向上方法および安定化方法
JPH07316065A (ja) * 1994-05-25 1995-12-05 Fujisawa Pharmaceut Co Ltd Ｆｒ９０１４６９物質製剤
WO1996006068A1 (fr) * 1994-08-22 1996-02-29 Yoshitomi Pharmaceutical Industries, Ltd. Compose benzenique et son utilisation medicale
JPH08175985A (ja) * 1994-12-26 1996-07-09 Lion Corp 点眼剤
WO1997024112A1 (fr) * 1995-12-28 1997-07-10 Yoshitomi Pharmaceutical Industries, Ltd. Preparation a usage externe

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS58148816A (ja) * 1982-02-27 1983-09-05 Nippon Zenyaku Kogyo Kk 低刺激性チアムリン注射剤
JPH05213757A (ja) * 1990-08-13 1993-08-24 Senju Pharmaceut Co Ltd 水性液剤
JPH0616547A (ja) * 1992-07-01 1994-01-25 Wakamoto Pharmaceut Co Ltd 消炎点眼剤
WO1994008943A1 (fr) * 1992-10-21 1994-04-28 Yoshitomi Pharmaceutical Industries, Ltd. Compose 2-amino-1,3-propanediol et immunosuppresseur
JPH07228532A (ja) * 1993-04-22 1995-08-29 Senju Pharmaceut Co Ltd 水性液剤、その有効成分の溶解性向上方法および安定化方法
JPH07316065A (ja) * 1994-05-25 1995-12-05 Fujisawa Pharmaceut Co Ltd Ｆｒ９０１４６９物質製剤
WO1996006068A1 (fr) * 1994-08-22 1996-02-29 Yoshitomi Pharmaceutical Industries, Ltd. Compose benzenique et son utilisation medicale
JPH08175985A (ja) * 1994-12-26 1996-07-09 Lion Corp 点眼剤
WO1997024112A1 (fr) * 1995-12-28 1997-07-10 Yoshitomi Pharmaceutical Industries, Ltd. Preparation a usage externe

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1312359A2 (fr) * 1996-11-19 2003-05-21 Novartis AG Utilisation de derives de 1,3-propanediol
EP1312359A3 (fr) * 1996-11-19 2004-01-02 Novartis AG Utilisation de derives de 1,3-propanediol
WO1998037875A1 (fr) * 1997-02-27 1998-09-03 Yoshitomi Pharmaceutical Industries, Ltd. Composition medicamenteuse
WO1999036065A1 (fr) * 1998-01-19 1999-07-22 Yoshitomi Pharmaceutical Industries, Ltd. Compositions medicinales
WO2001001978A1 (fr) * 1999-06-30 2001-01-11 Mitsubishi Pharma Corporation Compositions de medicaments servant a prevenir ou a traiter la myocardite virale
AU770495B2 (en) * 1999-06-30 2004-02-26 Akira Matsumori Medicinal compositions for preventing or treating viral myocarditis
US7902261B2 (en) 1999-06-30 2011-03-08 Mitsubishi Tanabe Pharma Corporation Medicinal compositions for preventing or treating viral myocarditis
US6423739B1 (en) 2000-02-23 2002-07-23 Daiichi Pharmaceutical Co., Ltd. Method for aiding cerebral recovery following neurodegeneration
US6437165B1 (en) 2000-08-31 2002-08-20 Merck & Co., Inc. Phosphate derivatives as immunoregulatory agents
US8324283B2 (en) 2003-04-08 2012-12-04 Novartis Ag Solid pharmaceutical compositions comprising a SIP receptor agonist and a sugar alcohol

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Publication number Publication date
AU3460897A (en) 1998-02-10
JP2002241272A (ja) 2002-08-28

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