NO313179B1 - Anvendelse av en insulinsensibilisator for fremstilling av et preparat for behandling og profylakse av pankreatitt - Google Patents

Anvendelse av en insulinsensibilisator for fremstilling av et preparat for behandling og profylakse av pankreatitt Download PDF

Info

Publication number: NO313179B1
Authority: NO; Norway
Prior art keywords: group; denotes; carbon atoms; hydrogen atom; use according
Prior art date: 1996-03-18

Application number

NO19971219A

Other languages

English (en)

Norwegian (no)

Other versions

NO971219L (no

NO971219D0 (no

Inventor

Toshihiko Fujiwara

Hiroyoshi Horikoshi

Masaharu Fukami

Original Assignee

Sankyo Co

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.)

1996-03-18

Filing date

1997-03-17

Publication date

2002-08-26

1997-03-17 Application filed by Sankyo Co filed Critical Sankyo Co

1997-03-17 Publication of NO971219D0 publication Critical patent/NO971219D0/no

1997-09-19 Publication of NO971219L publication Critical patent/NO971219L/no

2002-08-26 Publication of NO313179B1 publication Critical patent/NO313179B1/no

Links

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230000007935 neutral effect Effects 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
235000016709 nutrition Nutrition 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical class CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
235000020830 overeating Nutrition 0.000 description 1
229940116315 oxalic acid Drugs 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
125000001148 pentyloxycarbonyl group Chemical group 0.000 description 1
239000002304 perfume Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910000160 potassium phosphate Inorganic materials 0.000 description 1
235000011009 potassium phosphates Nutrition 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
229940002612 prodrug Drugs 0.000 description 1
239000000651 prodrug Substances 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
235000018102 proteins Nutrition 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
125000001453 quaternary ammonium group Chemical group 0.000 description 1
230000008929 regeneration Effects 0.000 description 1
238000011069 regeneration method Methods 0.000 description 1
230000028327 secretion Effects 0.000 description 1
231100000489 sensitizer Toxicity 0.000 description 1
230000001235 sensitizing effect Effects 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
239000004208 shellac Substances 0.000 description 1
235000013874 shellac Nutrition 0.000 description 1
229940113147 shellac Drugs 0.000 description 1
235000020374 simple syrup Nutrition 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
235000010413 sodium alginate Nutrition 0.000 description 1
239000000661 sodium alginate Substances 0.000 description 1
229940005550 sodium alginate Drugs 0.000 description 1
239000012453 solvate Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
239000007940 sugar coated tablet Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
238000002636 symptomatic treatment Methods 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
229960001367 tartaric acid Drugs 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
150000003548 thiazolidines Chemical class 0.000 description 1
125000001984 thiazolidinyl group Chemical group 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
230000000472 traumatic effect Effects 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
239000012588 trypsin Substances 0.000 description 1
208000001072 type 2 diabetes mellitus Diseases 0.000 description 1
210000002700 urine Anatomy 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
230000003313 weakening effect Effects 0.000 description 1

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
- A61K31/33—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
- A61K31/425—Thiazoles
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
- 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
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
- 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
- A61K31/42—Oxazoles
- 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
- A61K31/425—Thiazoles
- A61K31/427—Thiazoles not condensed and containing further heterocyclic rings
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/18—Drugs for disorders of the alimentary tract or the digestive system for pancreatic disorders, e.g. pancreatic enzymes

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Epidemiology (AREA)
Chemical Kinetics & Catalysis (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Thiazole And Isothizaole Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Catching Or Destruction (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Superconductors And Manufacturing Methods Therefor (AREA)

NO19971219A 1996-03-18 1997-03-17 Anvendelse av en insulinsensibilisator for fremstilling av et preparat for behandling og profylakse av pankreatitt NO313179B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP6106396		1996-03-18
JP25020196		1996-09-20

Publications (3)

Publication Number	Publication Date
NO971219D0 NO971219D0 (no)	1997-03-17
NO971219L NO971219L (no)	1997-09-19
NO313179B1 true NO313179B1 (no)	2002-08-26

Family

ID=26402115

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO19971219A NO313179B1 (no)	1996-03-18	1997-03-17	Anvendelse av en insulinsensibilisator for fremstilling av et preparat for behandling og profylakse av pankreatitt

Country Status (19)

Country	Link
US (1)	US5753681A (de)
EP (1)	EP0796618B1 (de)
KR (1)	KR100542778B1 (de)
CN (1)	CN1178657C (de)
AT (1)	ATE212548T1 (de)
AU (1)	AU708315B2 (de)
CA (1)	CA2200126C (de)
CZ (1)	CZ283968B6 (de)
DE (1)	DE69710111T2 (de)
DK (1)	DK0796618T3 (de)
ES (1)	ES2167678T3 (de)
HK (1)	HK1003051A1 (de)
HU (1)	HUP9700598A3 (de)
ID (1)	ID16266A (de)
IL (1)	IL120443A (de)
NO (1)	NO313179B1 (de)
NZ (1)	NZ314406A (de)
PT (1)	PT796618E (de)
TW (1)	TW548102B (de)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB9711683D0 (en) *	1997-06-05	1997-08-06	Smithkline Beecham Plc	Composition
CN1255386C (zh) *	1997-10-08	2006-05-10	三共株式会社	有取代稠合杂环化合物
SK161499A3 (en)	1998-03-30	2000-06-12	Japan Tobacco Inc	Process for producing isooxazolidinedione compound
US7045519B2 (en) *	1998-06-19	2006-05-16	Chiron Corporation	Inhibitors of glycogen synthase kinase 3
JP4533534B2 (ja)	1998-06-19	2010-09-01	ノバルティスバクシンズアンドダイアグノスティックス，インコーポレーテッド	グリコーゲンシンターゼキナーゼ３のインヒビター
IL140664A0 (en) *	1998-07-21	2002-02-10	Smithkline Beecham Plc	Use of glucose uptake enhancer for reducing apoptosis
US20040102486A1 (en) *	1998-11-12	2004-05-27	Smithkline Beecham Corporation	Novel method of treatment
US20030153607A1 (en) *	1998-11-12	2003-08-14	Smithkline Beecham P.L.C.	Novel composition and use
WO2001000223A2 (en) *	1999-06-25	2001-01-04	Minimed Inc.	Multiple agent diabetes therapy
EP1213287B1 (de)	1999-08-23	2005-05-25	Kyorin Pharmaceutical Co., Ltd.	Substituierte benzylthiazolidin-2,4-dion-derivate
DE60020573T2 (de)	1999-08-23	2006-03-16	Kyorin Pharmaceutical Co., Ltd.	Substituierte benzylthiazolidin-2,4-dion derivate
US6452014B1 (en) *	2000-12-22	2002-09-17	Geron Corporation	Telomerase inhibitors and methods of their use
US6852694B2 (en)	2001-02-21	2005-02-08	Medtronic Minimed, Inc.	Stabilized insulin formulations
US6737401B2 (en)	2001-06-28	2004-05-18	Metronic Minimed, Inc.	Methods of evaluating protein formulation stability and surfactant-stabilized insulin formulations derived therefrom
MA33248B1 (fr)	2009-04-01	2012-05-02	Genentech Inc	Traitement de troubles résistant à l'insuline

Family Cites Families (20)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5522636A (en) *	1978-08-04	1980-02-18	Takeda Chem Ind Ltd	Thiazoliding derivative
JPS6051189A (ja) *	1983-08-30	1985-03-22	Sankyo Co Ltd	チアゾリジン誘導体およびその製造法
DE3343141A1 (de) *	1983-11-29	1985-06-05	Hermann P.T. 7400 Tübingen Ammon	Verwendung von cystein-derivaten oder deren salzen, zur steigerung der insulinsekretion der langerhans'schen inseln der bauchspeicheldruese
CN1003445B (zh) *	1984-10-03	1989-03-01	武田药品工业株式会社	噻唑烷二酮衍生物，其制备方法和用途
AR240698A1 (es) *	1985-01-19	1990-09-28	Takeda Chemical Industries Ltd	Procedimiento para preparar compuestos de 5-(4-(2-(5-etil-2-piridil)-etoxi)benzil)-2,4-tiazolidindiona y sus sales
US4703052A (en) *	1985-05-21	1987-10-27	Pfizer Inc.	Hypoglycemic thiazolidinediones
US5194443A (en) *	1987-09-04	1993-03-16	Beecham Group P.L.C.	Compounds
US5232925A (en) *	1987-09-04	1993-08-03	Beecham Group P.L.C.	Compounds
ATE186724T1 (de) *	1987-09-04	1999-12-15	Beecham Group Plc	Substituierte thiazolidindionderivate
US5260445A (en) *	1987-09-04	1993-11-09	Beecham Group P.L.C.	2,4-thiazolidinediones
MX15171A (es) *	1988-03-08	1993-05-01	Pfizer	Derivados de tiazolidinodiona hipoglicemicos
DK375789A (da) *	1988-08-18	1990-02-19	Syntex Inc	Peptidderivater
JP2845743B2 (ja) *	1992-12-28	1999-01-13	三菱化学株式会社	新規なナフタレン誘導体
AU7118694A (en) *	1993-07-13	1995-02-13	Janica M. Moizis	Fastener for clothing
DK0684242T3 (da) *	1993-12-27	1999-11-01	Japan Tobacco Inc	Isoxazolidindionderivat og anvendelse deraf
NO305987B1 (no) *	1994-04-11	1999-08-30	Sankyo Co	Heterosykliske forbindelser med antidiabetisk aktivitet, deres anvendelse og farmasoeytisk preparat inneholdende disse
US5594015A (en) *	1994-06-22	1997-01-14	Regents Of The University Of California	Thiazolidine derivatives for the treatment of psoriasis
FR2721608B1 (fr) *	1994-06-22	1996-07-19	Rhone Poulenc Rorer Sa	Dérivés de thiazolidine, leur préparation et les médicaments les contenant.
US5703096A (en) *	1994-10-07	1997-12-30	Sankyo Company, Limited	Oxime derivatives, their preparation and their therapeutic use
CZ293016B6 (cs) *	1995-06-01	2004-01-14	Sankyo Company Limited	Benzimidazolové deriváty a farmaceutické prostředky s jejich obsahem

1997
- 1997-03-13 NZ NZ314406A patent/NZ314406A/xx unknown
- 1997-03-13 IL IL12044397A patent/IL120443A/xx not_active IP Right Cessation
- 1997-03-14 ID IDP970826A patent/ID16266A/id unknown
- 1997-03-14 CZ CZ97790A patent/CZ283968B6/cs unknown
- 1997-03-17 NO NO19971219A patent/NO313179B1/no unknown
- 1997-03-17 CA CA002200126A patent/CA2200126C/en not_active Expired - Fee Related
- 1997-03-17 ES ES97301773T patent/ES2167678T3/es not_active Expired - Lifetime
- 1997-03-17 DE DE69710111T patent/DE69710111T2/de not_active Expired - Fee Related
- 1997-03-17 US US08/819,686 patent/US5753681A/en not_active Expired - Fee Related
- 1997-03-17 HU HU9700598A patent/HUP9700598A3/hu unknown
- 1997-03-17 AU AU16285/97A patent/AU708315B2/en not_active Ceased
- 1997-03-17 EP EP97301773A patent/EP0796618B1/de not_active Expired - Lifetime
- 1997-03-17 DK DK97301773T patent/DK0796618T3/da active
- 1997-03-17 TW TW086103285A patent/TW548102B/zh not_active IP Right Cessation
- 1997-03-17 AT AT97301773T patent/ATE212548T1/de not_active IP Right Cessation
- 1997-03-17 PT PT97301773T patent/PT796618E/pt unknown
- 1997-03-18 KR KR1019970009207A patent/KR100542778B1/ko not_active IP Right Cessation
- 1997-03-18 CN CNB971112118A patent/CN1178657C/zh not_active Expired - Fee Related
1998
- 1998-03-16 HK HK98102164A patent/HK1003051A1/xx not_active IP Right Cessation

Also Published As

Publication number	Publication date
IL120443A (en)	2000-07-16
NO971219L (no)	1997-09-19
EP0796618B1 (de)	2002-01-30
HU9700598D0 (en)	1997-05-28
ES2167678T3 (es)	2002-05-16
CN1178657C (zh)	2004-12-08
HK1003051A1 (en)	1998-10-09
DE69710111T2 (de)	2002-10-02
US5753681A (en)	1998-05-19
IL120443A0 (en)	1997-07-13
EP0796618A1 (de)	1997-09-24
NO971219D0 (no)	1997-03-17
HUP9700598A2 (hu)	1998-09-28
CZ79097A3 (en)	1997-10-15
CA2200126C (en)	2006-08-15
HUP9700598A3 (en)	1998-10-28
KR100542778B1 (ko)	2006-04-14
CZ283968B6 (cs)	1998-07-15
PT796618E (pt)	2002-06-28
ID16266A (id)	1997-09-18
DK0796618T3 (da)	2002-05-06
TW548102B (en)	2003-08-21
CA2200126A1 (en)	1997-09-18
KR19980023975A (ko)	1998-07-06
AU708315B2 (en)	1999-07-29
DE69710111D1 (de)	2002-03-14
MX9702058A (es)	1998-03-31
AU1628597A (en)	1997-09-25
NZ314406A (en)	2000-12-22
CN1170575A (zh)	1998-01-21
ATE212548T1 (de)	2002-02-15

Publication	Publication Date	Title
NO313179B1 (no)	2002-08-26	Anvendelse av en insulinsensibilisator for fremstilling av et preparat for behandling og profylakse av pankreatitt
AU706628B2 (en)	1999-06-17	Treatment of arteriosclerosis and xanthoma
EP1637138A2 (de)	2006-03-22	Verwendung von Thiazolidindionen zur Vorbeugung oder Verzögerung des Auftretens des nichtinsulinabhängigen Diabetes Mellitus
RU2146521C1 (ru)	2000-03-20	Применение производных тиазолидина для лечения и профилактики остеопороза
KR20030016218A (ko)	2003-02-26	티아졸, 이미다졸 및 옥사졸 화합물, 및 단백질 노화와관련된 장애의 치료
CA2171827C (en)	2004-06-29	Use of thiazolidinediones to prevent or delay onset of niddm
JP2004518652A (ja)	2004-06-24	新規治療
US20070287685A1 (en)	2007-12-13	Medicinal composition containing FBPase inhibitor
JP3651816B2 (ja)	2005-05-25	動脈硬化症予防および治療剤
JP3968388B2 (ja)	2007-08-29	膵炎治療剤
RU2167656C2 (ru)	2001-05-27	Применение инсулинового сенсибилизатора для лечения и профилактики панкреатита
WO1997005875A2 (en)	1997-02-20	A method of reducing the amount of exogenous insulin administered to a patient having noninsulin-dependent diabetes mellitus
KR20070011497A (ko)	2007-01-24	각결막 장해 치료제
MXPA97002058A (en)	1998-10-15	Treatment and profilaxis of pancreati
AU750615B2 (en)	2002-07-25	Use of thiazolidinediones to prevent or delay onset of NIDDM
WO1997018811A1 (en)	1997-05-29	A method of treating myotonic dystrophy
AU749416B2 (en)	2002-06-27	Use of thiazolidinediones to prevent or delay onset of NIDDM
MXPA96002577A (en)	1998-01-01	Treatment of arterioesclerosis and xant
EA002659B1 (ru)	2002-08-29	Применение 5-[4-[2-(n-метил-n-(2-пиридил)амино)этокси]бензил]тиазолидин-2,4-диона для лечения гипергликемии
JPH09235229A (ja)	1997-09-09	骨粗鬆症治療剤
JP2006193516A (ja)	2006-07-27	ＦＢＰａｓｅ阻害剤を含有する医薬組成物