NO322500B1 - Oksa- og tiadiazol-derivater, farmasoytiske sammensetninger og kombinasjoner inneholdende disse forbindelsene og deres anvendelse for fremstilling av medikamenter for behandling av sykdommer - Google Patents

Oksa- og tiadiazol-derivater, farmasoytiske sammensetninger og kombinasjoner inneholdende disse forbindelsene og deres anvendelse for fremstilling av medikamenter for behandling av sykdommer Download PDF

Info

Publication number: NO322500B1
Authority: NO; Norway
Prior art keywords: mmol; compound; alkyl; solution; give
Prior art date: 1999-09-22

Application number

NO20021408A

Other languages

English (en)

Norwegian (no)

Other versions

NO20021408D0 (no

NO20021408L (no

Inventor

Peter T W Cheng

Pratik Devasthale

Yoon T Jeon

Sean Chen

Hao Zhang

Original Assignee

Bristol Myers Squibb 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.)

1999-09-22

Filing date

2002-03-21

Publication date

2006-10-16

2002-03-21 Application filed by Bristol Myers Squibb Co filed Critical Bristol Myers Squibb Co

2002-03-21 Publication of NO20021408D0 publication Critical patent/NO20021408D0/no

2002-05-14 Publication of NO20021408L publication Critical patent/NO20021408L/no

2006-10-16 Publication of NO322500B1 publication Critical patent/NO322500B1/no

Links

150000001875 compounds Chemical class 0.000 title claims description 466
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201000010099 disease Diseases 0.000 title claims description 13
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims description 13
238000004519 manufacturing process Methods 0.000 title claims description 7
239000008194 pharmaceutical composition Substances 0.000 title description 3
WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 title description 2
150000004867 thiadiazoles Chemical class 0.000 title description 2
-1 alkenyloksykarbonyl Chemical group 0.000 claims description 218
239000000460 chlorine Substances 0.000 claims description 150
239000000203 mixture Substances 0.000 claims description 128
125000000217 alkyl group Chemical group 0.000 claims description 116
125000003118 aryl group Chemical group 0.000 claims description 83
125000004432 carbon atom Chemical group C* 0.000 claims description 67
125000001424 substituent group Chemical group 0.000 claims description 50
150000002148 esters Chemical class 0.000 claims description 48
239000003112 inhibitor Substances 0.000 claims description 46
229920006395 saturated elastomer Polymers 0.000 claims description 46
125000000753 cycloalkyl group Chemical group 0.000 claims description 43
150000002367 halogens Chemical class 0.000 claims description 42
125000003545 alkoxy group Chemical group 0.000 claims description 41
229910052736 halogen Inorganic materials 0.000 claims description 36
125000001072 heteroaryl group Chemical group 0.000 claims description 32
125000003342 alkenyl group Chemical group 0.000 claims description 31
125000003710 aryl alkyl group Chemical group 0.000 claims description 30
229910052757 nitrogen Inorganic materials 0.000 claims description 28
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 27
125000000304 alkynyl group Chemical group 0.000 claims description 25
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125000001188 haloalkyl group Chemical group 0.000 claims description 18
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IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
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NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims description 16
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125000005236 alkanoylamino group Chemical group 0.000 claims description 12
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125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
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125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
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QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
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YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 claims description 7
239000004059 squalene synthase inhibitor Substances 0.000 claims description 7
125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
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PCZOHLXUXFIOCF-UHFFFAOYSA-N Monacolin X Natural products C12C(OC(=O)C(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 PCZOHLXUXFIOCF-UHFFFAOYSA-N 0.000 claims description 6
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YASAKCUCGLMORW-UHFFFAOYSA-N Rosiglitazone Chemical compound C=1C=CC=NC=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O YASAKCUCGLMORW-UHFFFAOYSA-N 0.000 claims description 6
239000000556 agonist Substances 0.000 claims description 6
125000003282 alkyl amino group Chemical group 0.000 claims description 6
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229910052794 bromium Inorganic materials 0.000 claims description 6
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 claims description 6
230000000694 effects Effects 0.000 claims description 6
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QLJODMDSTUBWDW-UHFFFAOYSA-N lovastatin hydroxy acid Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(C)C=C21 QLJODMDSTUBWDW-UHFFFAOYSA-N 0.000 claims description 6
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HYAFETHFCAUJAY-UHFFFAOYSA-N pioglitazone Chemical compound N1=CC(CC)=CC=C1CCOC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 HYAFETHFCAUJAY-UHFFFAOYSA-N 0.000 claims description 6
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 6
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims description 6
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ZGGHKIMDNBDHJB-NRFPMOEYSA-M (3R,5S)-fluvastatin sodium Chemical compound [Na+].C12=CC=CC=C2N(C(C)C)C(\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O)=C1C1=CC=C(F)C=C1 ZGGHKIMDNBDHJB-NRFPMOEYSA-M 0.000 claims description 5
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XUKUURHRXDUEBC-UHFFFAOYSA-N Atorvastatin Natural products C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CCC(O)CC(O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-UHFFFAOYSA-N 0.000 claims description 5
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RYMZZMVNJRMUDD-UHFFFAOYSA-N SJ000286063 Natural products C12C(OC(=O)C(C)(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 RYMZZMVNJRMUDD-UHFFFAOYSA-N 0.000 claims description 5
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VCKUSRYTPJJLNI-UHFFFAOYSA-N terazosin Chemical compound N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCN1C(=O)C1CCCO1 VCKUSRYTPJJLNI-UHFFFAOYSA-N 0.000 description 1
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JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
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Classifications

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- C07—ORGANIC CHEMISTRY
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- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/32—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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- A61P17/06—Antipsoriatics
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
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- A61P3/06—Antihyperlipidemics
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/48—Drugs for disorders of the endocrine system of the pancreatic hormones
- A61P5/50—Drugs for disorders of the endocrine system of the pancreatic hormones for increasing or potentiating the activity of insulin
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/24—Radicals substituted by oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems

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NO20021408A 1999-09-22 2002-03-21 Oksa- og tiadiazol-derivater, farmasoytiske sammensetninger og kombinasjoner inneholdende disse forbindelsene og deres anvendelse for fremstilling av medikamenter for behandling av sykdommer NO322500B1 (no)

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Application Number	Priority Date	Filing Date	Title
US15540099P	1999-09-22	1999-09-22
PCT/US2000/025710 WO2001021602A1 (en)	1999-09-22	2000-09-19	Oxa- and thiazole derivatives useful as antidiabetic and antiobesity agents

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Publication Number	Publication Date
NO20021408D0 NO20021408D0 (no)	2002-03-21
NO20021408L NO20021408L (no)	2002-05-14
NO322500B1 true NO322500B1 (no)	2006-10-16

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US (1)	US7579479B2 (es)
EP (1)	EP1218361B1 (es)
JP (2)	JP4332315B2 (es)
KR (1)	KR100682419B1 (es)
CN (1)	CN1289490C (es)
AR (1)	AR025756A1 (es)
AT (1)	ATE420080T1 (es)
AU (1)	AU782031B2 (es)
BR (1)	BR0014189A (es)
CA (1)	CA2388452C (es)
CO (1)	CO5200832A1 (es)
DE (1)	DE60041343D1 (es)
EG (1)	EG24169A (es)
ES (1)	ES2319097T3 (es)
HK (1)	HK1049337B (es)
HU (1)	HUP0204416A3 (es)
IL (2)	IL147939A0 (es)
MX (1)	MXPA02001847A (es)
MY (1)	MY138525A (es)
NO (1)	NO322500B1 (es)
NZ (1)	NZ516820A (es)
PE (1)	PE20010643A1 (es)
PL (1)	PL364986A1 (es)
RU (2)	RU2279427C2 (es)
TR (1)	TR200200732T2 (es)
TW (4)	TW200528436A (es)
WO (1)	WO2001021602A1 (es)
ZA (1)	ZA200200937B (es)

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2000
- 2000-09-18 TW TW093126011A patent/TW200528436A/zh unknown
- 2000-09-18 TW TW089119155A patent/TWI260321B/zh not_active IP Right Cessation
- 2000-09-18 TW TW094102034A patent/TWI302149B/zh not_active IP Right Cessation
- 2000-09-18 TW TW093126012A patent/TW200514783A/zh unknown
- 2000-09-19 RU RU2002108928/04A patent/RU2279427C2/ru not_active IP Right Cessation
- 2000-09-19 IL IL14793900A patent/IL147939A0/xx active IP Right Grant
- 2000-09-19 HU HU0204416A patent/HUP0204416A3/hu unknown
- 2000-09-19 ES ES00965172T patent/ES2319097T3/es not_active Expired - Lifetime
- 2000-09-19 WO PCT/US2000/025710 patent/WO2001021602A1/en not_active Ceased
- 2000-09-19 BR BR0014189-5A patent/BR0014189A/pt not_active Application Discontinuation
- 2000-09-19 NZ NZ516820A patent/NZ516820A/en unknown
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- 2000-09-19 KR KR1020027003723A patent/KR100682419B1/ko not_active Expired - Fee Related
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- 2000-09-19 RU RU2005117879/04A patent/RU2327692C2/ru not_active IP Right Cessation
- 2000-09-19 EG EG20001198A patent/EG24169A/xx active
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- 2000-09-19 CN CNB008131406A patent/CN1289490C/zh not_active Expired - Fee Related
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- 2000-09-22 PE PE2000000994A patent/PE20010643A1/es not_active Application Discontinuation
- 2000-09-22 AR ARP000104989A patent/AR025756A1/es not_active Application Discontinuation
2002
- 2002-01-31 IL IL147939A patent/IL147939A/en not_active IP Right Cessation
- 2002-02-01 ZA ZA200200937A patent/ZA200200937B/en unknown
- 2002-03-21 NO NO20021408A patent/NO322500B1/no not_active IP Right Cessation
2005
- 2005-08-22 US US11/155,965 patent/US7579479B2/en not_active Expired - Lifetime
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Also Published As

Publication number	Publication date
KR20020047179A (ko)	2002-06-21
KR100682419B1 (ko)	2007-02-28
CA2388452A1 (en)	2001-03-29
IL147939A (en)	2008-03-20
WO2001021602A1 (en)	2001-03-29
IL147939A0 (en)	2002-08-14
NO20021408D0 (no)	2002-03-21
TW200538446A (en)	2005-12-01
TR200200732T2 (tr)	2002-10-21
PL364986A1 (en)	2004-12-27
ES2319097T3 (es)	2009-05-04
ZA200200937B (en)	2003-07-30
JP4332315B2 (ja)	2009-09-16
CA2388452C (en)	2007-04-03
RU2002108928A (ru)	2004-01-10
RU2279427C2 (ru)	2006-07-10
HUP0204416A3 (en)	2006-01-30
AU7593500A (en)	2001-04-24
CN1289490C (zh)	2006-12-13
HK1049337A1 (en)	2003-05-09
HUP0204416A2 (hu)	2003-04-28
TWI302149B (en)	2008-10-21
AU782031B2 (en)	2005-06-30
MY138525A (en)	2009-06-30
US20070015797A1 (en)	2007-01-18
BR0014189A (pt)	2002-08-20
EG24169A (en)	2008-09-10
HK1049337B (zh)	2007-07-27
CO5200832A1 (es)	2002-09-27
ATE420080T1 (de)	2009-01-15
NZ516820A (en)	2004-11-26
EP1218361A1 (en)	2002-07-03
TWI260321B (en)	2006-08-21
JP2003509503A (ja)	2003-03-11
RU2327692C2 (ru)	2008-06-27
CN1374955A (zh)	2002-10-16
RU2005117879A (ru)	2006-11-20
TW200528436A (en)	2005-09-01
NO20021408L (no)	2002-05-14
EP1218361B1 (en)	2009-01-07
TW200514783A (en)	2005-05-01
MXPA02001847A (es)	2002-10-23
DE60041343D1 (de)	2009-02-26
JP2009102360A (ja)	2009-05-14
PE20010643A1 (es)	2001-08-18
US7579479B2 (en)	2009-08-25
AR025756A1 (es)	2002-12-11

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Publication	Publication Date	Title
US6727271B2 (en)	2004-04-27	Substituted acid derivatives useful as antidiabetic and antiobesity agents and method
RU2279427C2 (ru)	2006-07-10	Окса- и тиазолпроизводные в качестве антидиабетических агентов и агентов против ожирения
US6673815B2 (en)	2004-01-06	Substituted acid derivatives useful as antidiabetic and antiobesity agents and method
EP1401433B1 (en)	2010-11-10	Azole acid derivatives, alone or in combination, for treating diabetes and dyslipidemias; and for treating malignant diseases
EP1531810B1 (en)	2012-02-01	Substituted heterocyclic derivatives useful as antidiabetic and antiobesity agents and method
EP1589006A1 (en)	2005-10-26	Oxa- and thiazole derivatives useful as antidiabetics and antidiobesity agents
HK1078584A (en)	2006-03-17	Oxa- and thiazole derivatives useful as antidiabetics and antidiobesity agents