WO2006126625A1 - ピラゾロン誘導体を含む医薬 - Google Patents
ピラゾロン誘導体を含む医薬 Download PDFInfo
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- WO2006126625A1 WO2006126625A1 PCT/JP2006/310425 JP2006310425W WO2006126625A1 WO 2006126625 A1 WO2006126625 A1 WO 2006126625A1 JP 2006310425 W JP2006310425 W JP 2006310425W WO 2006126625 A1 WO2006126625 A1 WO 2006126625A1
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- carbon atoms
- antibiotic
- alkyl
- group
- administration
- Prior art date
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Classifications
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- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
- A61K31/4152—1,2-Diazoles having oxo groups directly attached to the heterocyclic ring, e.g. antipyrine, phenylbutazone, sulfinpyrazone
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
- A61K31/542—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame ortho- or peri-condensed with heterocyclic ring systems
- A61K31/545—Compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins, cefaclor, or cephalexine
- A61K31/546—Compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins, cefaclor, or cephalexine containing further heterocyclic rings, e.g. cephalothin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Definitions
- a pyrazolone derivative or a physiologically acceptable salt thereof, or a hydrate or solvate thereof (hereinafter, these may be collectively referred to simply as a pyrazolone derivative) is an active ingredient. It is related with the medicine containing.
- R 1 represents a hydrogen atom, aryl, alkyl having 1 to 5 carbon atoms, or an alkoxycarboxylic alkyl having 3 to 6 carbon atoms in total
- R 2 represents a hydrogen atom, aryloxy, aryl carbonate, carbon number 1 to 5 represents alkyl of 1 to 3 or hydroxyalkyl of 1 to 3, or R 1 and R 2 together represent alkylene of 3 to 5 carbon atoms
- R 3 represents a hydrogen atom, alkyl of 1 to 5 carbon atoms, Cycloalkyl having 5 to 7 carbon atoms, hydroxyalkyl having 1 to 3 carbon atoms, benzyl, naphthyl or phenyl, or alkoxy having 1 to 5 carbon atoms, hydroxyalkyl having 1 to 3 carbon atoms, total carbon number 2 to 5 alkoxy carbonyl, 1 to 3 alkyl mercapto, 1 to 4 alkyl amide-containing total alkyl 2 to 8 dialkyl amide
- edaravone is a free radical scavenger that works to prevent cell damage by eliminating various free radicals including active oxygen.
- edaravone described above When edaravone described above is administered to cerebral infarction patients as a cerebral protectant, it may be administered in combination with antibiotics. Evidence of edaravone and antibiotics has been sufficiently studied so far. I was impressed.
- the object of the present invention is to use a dosage form that can alleviate renal damage and Z or renal dysfunction that are exacerbated when a combination of a virazolone derivative represented by the above formula (I) and an antibiotic is administered. It is to provide a medicine to be used.
- the present inventors administered a pyrazolone derivative represented by the formula (I) and an antibiotic (cephalothin) to rats by various administration modes, to thereby obtain kidney (function).
- a pyrazolone derivative represented by the formula (I) and an antibiotic (cephalothin) to rats by various administration modes, to thereby obtain kidney (function).
- the exacerbation of renal (function) disorder observed when the pyrazolone derivative represented by the formula (I) is combined with a renal excretion type antibiotic (cephalothin) was administered with the pyrazolone derivative represented by the formula (I) first. It was found that the case where the investment was made at the same time and after that appears more strongly than the case where it was done.
- R 1 represents a hydrogen atom, aryl, alkyl having 1 to 5 carbon atoms, or an alkoxycarboxylic alkyl having 3 to 6 carbon atoms in total
- R 2 represents a hydrogen atom, aryloxy, aryl carbonate, carbon number 1 to 5 represents alkyl or hydroxyalkyl having 1 to 3 carbon atoms, or R 1 and R 2 together represent alkylene having 3 to 5 carbon atoms
- R 3 represents a hydrogen atom, alkyl having 1 to 5 carbon atoms , Cycloalkyl having 5 to 7 carbon atoms, hydroxyalkyl having 1 to 3 carbon atoms, benzyl, naphthyl or phenol, alkoxy having 1 to 5 carbon atoms, hydroxyalkyl having 1 to 3 carbon atoms, total carbon number 2 to 5 alkoxy carbonyl, 1 to 3 carbon alkyl mercapto, 1 to 4 carbon atoms containing alkylamido 2 to 8 dialkylamino
- a brain protecting agent for patients to whom antibiotics are administered comprising as an active ingredient a pyrazolone derivative represented by the above or a physiologically acceptable salt thereof, or a hydrate or solvate thereof,
- a brain protective agent characterized by administering an antibiotic after administering a pyrazolone derivative or a physiologically acceptable salt thereof, or a hydrate or solvate thereof.
- a pyrazolone derivative represented by the above formula (I) or a physiologically acceptable salt thereof, or a hydrate or solvate thereof is contained as an active ingredient.
- An antibiotic is administered to a patient who is administered an antibiotic, and the antibiotic is administered after the administration of the pyrazolone derivative or a physiologically acceptable salt thereof, or a hydrate or solvate thereof, Provided is an agent for reducing renal damage exacerbated by the combined use of a pyrazolone derivative and an antibiotic.
- a pyrazolone derivative represented by the above formula (I) or a physiologically acceptable salt thereof, or a hydrate or solvate thereof is used as an active ingredient. And is administered to a patient who receives antibiotics, and the antibiotic is administered after administering the pyrazolone derivative or a physiologically acceptable salt thereof, or a hydrate or solvate thereof. Further, there is provided an agent for alleviating exacerbation of renal dysfunction observed by simultaneous administration of the pyrazolone derivative or a physiologically acceptable salt thereof, or a hydrate or solvate thereof and an antibiotic.
- the brain protective agent of the present invention is preferably used as a medicine for treatment and Z or prevention of cerebrovascular disorder.
- the cerebrovascular disorder is cerebral infarction.
- the treatment of cerebrovascular disorder is an improvement of neurological symptoms, daily life movement disorder or dysfunction associated with acute stage of cerebral infarction.
- the antibiotic is a renal excretion type antibiotic.
- the antibiotic is an antibiotic having a cecum skeleton.
- the antibiotic is cephalothin sodium.
- the pyrazolone derivative of formula (I) is 3 methyl 1 phenyl 2 pyrazolin 5-one.
- 3-methyl-1-phenol-2 pyrazolin-5-one as an active ingredient is administered to a patient to be administered antibiotics
- 3-methyl-1-phenol-2 Luo 2 is an alleviation agent for exacerbation of renal dysfunction caused by simultaneous administration of methyl 1-phenol 2 virazoline 5 ON and antibiotics, characterized by administering antibiotics after pyrazoline 5 ON.
- an antibiotic is administered after administering the pyrazolone derivative represented by the above formula (I) or a physiologically acceptable salt thereof, or a hydrate or solvate thereof. And a method for reducing renal damage exacerbated by the combined use of the pyrazolone derivative and an antibiotic.
- an antibiotic after administration of the pyrazolone derivative represented by the above formula (I) or a physiologically acceptable salt thereof, or a hydrate or solvate thereof In combination with the above-mentioned pyrazolone derivatives or physiologically acceptable salts thereof, or hydrates or solvates thereof, and antibiotics A method is provided for reducing the exacerbation of renal dysfunction.
- the 3-methyl-1 phenol-2 pyrazoline-5-on comprising the administration of an antibiotic after the administration of 3-methyl-1-phenol-2 pyrazoline-5-one and Methods are provided to reduce the exacerbation of renal dysfunction observed with co-administration with antibiotics.
- a brain protective agent for a patient to which an antibiotic is administered the pyrazolone derivative or a physiologically acceptable salt thereof, or a hydrate thereof.
- a pyrazolone derivative represented by the above formula (I) or a physiologically acceptable salt thereof, or a hydration thereof for the production of a brain protective agent characterized by administering an antibiotic after administering a solvate Or use of solvates is provided.
- the brain protective agent provided by the present invention and a renal disorder and Z or renal dysfunction alleviating agent exacerbated by the combined use of a pyrazolone derivative represented by the above formula (I) and an antibiotic ( Hereinafter, these are collectively referred to as the medicament of the present invention), and the pyrazolone derivative represented by the formula (I) or a physiologically acceptable salt thereof as defined herein, or a hydrate or hydrate thereof, Solvates are included as active ingredients.
- the compound represented by the formula (I) used in the present invention may also have a structure represented by the following formula (1) or (1 ") due to tautomerism.
- a structure represented by the following formula (1) or (1 ) due to tautomerism.
- one of the tautomers is shown, but the existence of the following tautomers will be obvious to those skilled in the art:
- the following formula () or A compound represented by ( ⁇ ) or a physiologically acceptable salt thereof, or a hydrate or solvate thereof may be used as an active ingredient of the medicament of the present invention.
- the aryl group in the definition of R 1 is a monocyclic or polycyclic aryl group. Misalignment is acceptable.
- a substituent such as a phenyl group or a naphthyl group, an alkyl group such as a methyl group or a butyl group, an alkoxy group such as a methoxy group or a butoxy group, a halogen atom such as a chlorine atom, or a substituent such as a hydroxyl group.
- a phenol group a same applies to aryl moieties in other substituents having aryl moieties (such as aryloxy groups).
- the alkyl group having 1 to 5 carbon atoms in the definition of R 2 and R 3 may be either linear or branched. Examples thereof include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, and a pentyl group. The same applies to the alkyl moiety in other substituents having an alkyl moiety (alkoxycarboalkyl group).
- the alkylene group having 3 to 5 carbon atoms in the definition of R 1 and R 2 includes trimethylene group, tetramethylene group, pentamethylene group, methyltrimethylene group, etyltrimethylene group, dimethyltrimethylene group, methyltetramethylene group. A methylene group etc. are mentioned.
- the aryloxy group in the definition of R 2 includes p-methylphenoxy group, p-methoxyphenoxy group, p-chlorophenoxy group, p-hydroxyphenoxy group, and the like. Examples thereof include a felt mercapto group, p-methylphenol mercapto group, p-methoxyphenol mercapto group, p-chlorophenol mercapto group, p-hydroxyphenol mercapto group and the like.
- Examples of the hydroxyalkyl group having 1 to 3 carbon atoms in the definitions of R 2 and R 3 include a hydroxymethyl group, a 2-hydroxyethyl group, and a 3-hydroxypropyl group.
- Examples of the cycloalkyl group having 5 to 7 carbon atoms in the definition of R 3 include a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group.
- the alkoxy group having 1 to 5 carbon atoms in the substituent of the phenyl group includes a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, a pentyloxy group, and the like.
- the alkoxycarbon group having 2 to 5 total carbon atoms include methoxy Examples thereof include carbol group, ethoxycarbol group, propoxycarbol group, butoxycarbol group, etc.
- Examples of the alkyl mercapto group having 1 to 3 carbon atoms include methyl mercapto group, ethyl mercapto group, propyl mercapto group.
- Examples of the alkylamino group having 1 to 4 carbon atoms include a methylamino group, an ethylamino group, a propylamino group, and a butylamino group, and examples of the dialkylamino group having 2 to 8 carbon atoms include a dimethylamino group.
- Examples of the compound (I) suitably used as the active ingredient of the medicament of the present invention include the compounds shown below.
- a physiologically acceptable salt may be used in addition to the free form compound represented by the formula (I).
- Physiologically acceptable salts include salts with mineral acids such as hydrochloric acid, sulfuric acid, hydrobromide, phosphoric acid; methanesulfonic acid, ⁇ toluenesulfonic acid, acetic acid, oxalic acid, citrate, malic acid, Salts with organic acids such as fumaric acid; sodium, potassium Salts with alkali metals such as magnesium; salts with alkaline earth metals such as magnesium; salts with amines such as ammonia, ethanolamine, 2-amino-2-methyl-1-propanol, and the like.
- the type of salt is not particularly limited as long as it is physiologically acceptable.
- the dose of the medicament of the present invention is not particularly limited, but usually 0.1 to 100 mg / kg body weight per day in the case of oral administration generally as the weight of the compound represented by formula (I) which is an active ingredient. In the case of parenteral administration, it is 0.1 to 100 mg / kg body weight per day.
- the above dose may be increased or decreased as appropriate according to the age, pathologic condition and symptoms that it is preferable to administer once a day or divided into 2 to 3 times a day.
- the compound represented by the above formula (I) or a physiologically acceptable salt thereof, or a hydrate or solvate thereof may be administered as it is.
- a pharmaceutical composition containing the above-mentioned substance as an active ingredient and a pharmacologically and pharmaceutically acceptable additive.
- Examples of pharmacologically and pharmaceutically acceptable additives include excipients, disintegrants or disintegration aids, binders, lubricants, coating agents, dyes, diluents, and bases. , Solubilizers or solubilizers, tonicity agents, pH regulators, stabilizers, propellants, and adhesives can be used.
- compositions suitable for oral administration include, for example, excipients such as glucose, lactose, D-manntol, starch, or crystalline cellulose; carboxymethyl cellulose, starch, or Disintegrants or disintegration aids such as carboxymethylcellulose calcium; binders such as hydroxypropylcellulose, hydroxypropylmethylcellulose, polybulur pyrrolidone, or gelatin; lubricants such as magnesium stearate or talc; hydroxypropylmethylcellulose, sucrose, polyethylene glycol Alternatively, a coating agent such as titanium oxide; a base such as petrolatum, liquid paraffin, polyethylene glycol, gelatin, kaolin, glycerin, purified water, or hard fat can be used.
- excipients such as glucose, lactose, D-manntol, starch, or crystalline cellulose
- carboxymethyl cellulose, starch, or Disintegrants or disintegration aids such as carboxymethylcellulose calcium
- binders such as hydroxypropyl
- compositions suitable for injection or infusion include distilled water for injection, physiological saline, Solvents or solubilizers that can constitute aqueous or in-use soluble injections such as pyrendalicol; isotonic agents such as glucose, sodium chloride salt, D-manntol, glycerin; inorganic acids, organic acids
- an additive such as a pH regulator such as an inorganic base or an organic base can be used.
- the pharmaceutical form of the present invention is not particularly limited, and can take various forms available to those skilled in the art.
- pharmaceuticals suitable for oral administration for example, tablets, capsules, powders, fine granules, granules and the like can be prepared using solid pharmaceutical additives, and liquid pharmaceutical additives can be used. Syrups and the like can be prepared.
- injections, infusions, suppositories, transdermal absorption agents, and the like can be prepared as pharmaceuticals suitable for parenteral administration.
- the brain protective agent (instillation) containing the compound of formula (I) above as an active ingredient has already been used in clinical practice (generic name “Edaravone”, product name “Radicut”: The above-mentioned commercially available preparation can be used as it is in the pharmaceutical of the present invention manufactured and sold by Mitsubishi Welpharma Co., Ltd.
- the route of administration of the medicament of the present invention is not particularly limited, and can be administered orally or parenterally.
- the administration route for parenteral administration is not particularly limited, and can be administered intravenously or intraarterially.
- the medicament of the present invention is administered prior to antibiotic administration. That is, when this drug (that is, the pyrazolone derivative represented by the formula (I)) and an antibiotic are used in combination, it is desirable to avoid simultaneous administration as much as possible and administer this drug first. It is advisable to consider administering this drug first.
- the administration interval of the medicament of the present invention is not particularly limited as long as it is administered prior to administration of antibiotics, but is preferably 1 hour or more before administration of antibiotics, more preferably 2 hours. It can be administered before.
- the medicament of the present invention can be administered, for example, about 1 to 6 hours, more preferably about 2 to 6 hours, and particularly preferably 2 to 4 hours before the administration of antibiotics. Can be administered before.
- the type of antibiotic used in combination with the pyrazolone derivative represented by the formula (I) is not particularly limited, and examples thereof include renal excretion type antibiotics, antibiotics having a cefme skeleton, etc. Is mentioned. Specific examples of antibiotics include cefazolin sodium, salt Powers such as cefotiam acid, piperacillin sodium and the like are not limited to these.
- the subject of the administration of the medicament of the present invention is not particularly limited as long as it is a patient who can expect preventive and Z or therapeutic effects by eliminating various free radicals including active oxygen.
- the pyrazolone derivative represented by the formula (I) has both an EEG normalizing action and a cerebral ischemic protective action, and can also be administered orally, and cervical trauma.
- Treatment of intracerebral hemorrhage, cerebral arteriosclerosis, cerebral infarction, cerebral embolism, etc. treatment of ischemic cerebrovascular disorders such as cerebral edema caused by the disease in the acute phase, cerebrovascular disorder after prolonging the acute phase, Of various diseases observed in the subacute phase and chronic phase of the disease, for example, treatment of hypocerebral dysfunction represented by vascular dementia, prevention of recurrence, and development of various encephalopathy associated with progression of cerebral vascular tissue disease associated with aging It can be widely applied to treatment, clarification of turbidity appearing in the acute and chronic phases of cerebrovascular disorder, and anesthesia.
- renal disorder or renal dysfunction may include, for example, decreased urine output (oliguria), increased blood urea nitrogen (BUN), increased serum creatine, or renal failure.
- oliguria decreased urine output
- BUN blood urea nitrogen
- serum creatine increased serum creatine
- Group A group in which only cephalothin and glycerol are administered without edaravone
- Group B Group receiving edaravone, cephalothin and glycerol simultaneously
- Group C Group receiving cephalotin and glycerol 2 hours after edaravone administration
- Group D Group receiving cephalothin and glycerol 4 hours after edaravone administration
- Group E Group in which only cephalothin and glycerol are administered without edaravone
- Group F Group receiving edaravone, cephalothin and glycerol simultaneously
- Group G Group receiving cephalotin and glycerol 1 hour after edaravone administration
- Group H Group receiving cephalotin and glycerol one hour before edaravone administration
- Group I Group receiving cephalotin and glycerol 2 hours before edaravone administration
- Group E only cephalotin (2000 mgZkg) and glycerol (lgZkg) were administered simultaneously, and edaravone was not administered. The day after the above administration, each group of rats was dissected and a histopathological examination and morphometric analysis were performed in the same manner as in Test Example 1 (by preparing HE-stained specimens of kidney tissue).
- Test Example 1 The results of Test Example 1 and Test Example 2 are shown in Table 2 and Table 3 below.
- Cephalothin (mg / kg) 2000 2000 2000 2000 2000 2000 2000 Glyce mouth paste (g / kg) 1 1 1 1 1 1 Edaravone (I mg / g, bid) 0 200 200 200 200 Administration time difference (hours) 0 0 1 1 2 Findings (Number of cases) 10 10 10 10 10 10 10 10 10 10 10 10 10 Kidney (cortex) ⁇ 2 1 3 1 1 Proximal tubule + 8 5 7 2 7 Epithelial + + 0 0 4 0 6 2 Degeneration / necrosis + + + + + 0 0 0 1 0 ⁇ (Cortex) Disability score
- the medicament of the present invention it is possible to effectively reduce the renal disorder and Z or renal dysfunction that are exacerbated by the combined use of the pyrazolone derivative represented by the above formula (I) and an antibiotic. it can.
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- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
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Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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JP2007517887A JPWO2006126625A1 (ja) | 2005-05-25 | 2006-05-25 | ピラゾロン誘導体を含む医薬 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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JP2005152274 | 2005-05-25 | ||
JP2005-152274 | 2005-05-25 |
Publications (1)
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WO2006126625A1 true WO2006126625A1 (ja) | 2006-11-30 |
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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PCT/JP2006/310425 WO2006126625A1 (ja) | 2005-05-25 | 2006-05-25 | ピラゾロン誘導体を含む医薬 |
Country Status (3)
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JP (1) | JPWO2006126625A1 (ko) |
KR (1) | KR20080015123A (ko) |
WO (1) | WO2006126625A1 (ko) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20160280715A1 (en) * | 2011-12-21 | 2016-09-29 | Dan Theodorescu | Anti-cancer compounds targeting ral gtpases and methods of using the same |
US10676480B2 (en) | 2014-07-10 | 2020-06-09 | The Regents Of The University Of Colorado, A Body Corporate | Anti-cancer compounds targeting Ral GTPases and methods of using the same |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0531523B2 (ko) * | 1985-05-20 | 1993-05-12 | Mitsubishi Chem Ind | |
JPH0952831A (ja) * | 1995-08-10 | 1997-02-25 | Mitsubishi Chem Corp | 急性腎不全治療・予防剤 |
JP2004099560A (ja) * | 2002-09-11 | 2004-04-02 | Hiroshi Makino | 薬剤性腎障害の予防及び/又は治療のための医薬 |
JP2004300153A (ja) * | 2003-03-20 | 2004-10-28 | Kiyoshi Kurokawa | 蛋白修飾物生成抑制剤 |
-
2006
- 2006-05-25 WO PCT/JP2006/310425 patent/WO2006126625A1/ja active Application Filing
- 2006-05-25 KR KR1020077030067A patent/KR20080015123A/ko not_active Application Discontinuation
- 2006-05-25 JP JP2007517887A patent/JPWO2006126625A1/ja active Pending
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0531523B2 (ko) * | 1985-05-20 | 1993-05-12 | Mitsubishi Chem Ind | |
JPH0952831A (ja) * | 1995-08-10 | 1997-02-25 | Mitsubishi Chem Corp | 急性腎不全治療・予防剤 |
JP2004099560A (ja) * | 2002-09-11 | 2004-04-02 | Hiroshi Makino | 薬剤性腎障害の予防及び/又は治療のための医薬 |
JP2004300153A (ja) * | 2003-03-20 | 2004-10-28 | Kiyoshi Kurokawa | 蛋白修飾物生成抑制剤 |
Non-Patent Citations (1)
Title |
---|
IGUCHI T. ET AL.: "Edaravone inhibits acute renal injury and cyst formation in cisplatin-treated rat kidney", FREE RADICAL RESEARCH, vol. 38, no. 4, 2004, pages 333 - 341, XP003002765 * |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20160280715A1 (en) * | 2011-12-21 | 2016-09-29 | Dan Theodorescu | Anti-cancer compounds targeting ral gtpases and methods of using the same |
US10689392B2 (en) * | 2011-12-21 | 2020-06-23 | The Regents Of The University Of Colorado, A Body Corporate | Anti-cancer compounds targeting ral GTPases and methods of using the same |
US11964985B2 (en) | 2011-12-21 | 2024-04-23 | The Regents of the University of Colorado, a body corporate. | Anti-cancer compounds targeting Ral GTPases and methods of using the same |
US10676480B2 (en) | 2014-07-10 | 2020-06-09 | The Regents Of The University Of Colorado, A Body Corporate | Anti-cancer compounds targeting Ral GTPases and methods of using the same |
US11472812B2 (en) | 2014-07-10 | 2022-10-18 | The Regents Of The University Of Colorado, A Body Corporate | Anti-cancer compounds targeting Ral GTPases and methods of using the same |
Also Published As
Publication number | Publication date |
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KR20080015123A (ko) | 2008-02-18 |
JPWO2006126625A1 (ja) | 2008-12-25 |
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