OA12780A - Thiazole and oxazole derivatives which modulate PPAR activity. - Google Patents

Thiazole and oxazole derivatives which modulate PPAR activity. Download PDF

Info

Publication number: OA12780A
Authority: OA; OAPI
Prior art keywords: methyl; phenyl; compound; thiazol; hydrogen
Prior art date: 2002-03-07

Application number

OA1200400232A

Other languages

English (en)

Inventor

Xue-Min Cheng

Noe Ouano Erasga

Gary Frederick Filzen

Andrew George Geyer

Chitase Lee

Bharat Kalidas Trivedi

Original Assignee

Warner Lambert 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.)

2002-03-07

Filing date

2003-02-24

Publication date

2006-07-07

2003-02-24 Application filed by Warner Lambert Co filed Critical Warner Lambert Co

2006-07-07 Publication of OA12780A publication Critical patent/OA12780A/en

Links

230000000694 effects Effects 0.000 title abstract description 9
108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 title abstract description 5
102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 title abstract description 5
150000007978 oxazole derivatives Chemical class 0.000 title description 2
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 458
238000000034 method Methods 0.000 claims abstract description 30
208000031226 Hyperlipidaemia Diseases 0.000 claims abstract description 17
208000035150 Hypercholesterolemia Diseases 0.000 claims abstract description 12
241000124008 Mammalia Species 0.000 claims abstract description 11
150000003839 salts Chemical class 0.000 claims abstract description 9
239000001257 hydrogen Substances 0.000 claims description 128
229910052739 hydrogen Inorganic materials 0.000 claims description 128
-1 ethoxy, isopropoxy, n-propoxy, t-butoxy, n-butoxy Chemical group 0.000 claims description 96
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 80
125000000217 alkyl group Chemical group 0.000 claims description 68
150000002431 hydrogen Chemical class 0.000 claims description 53
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 37
125000000304 alkynyl group Chemical group 0.000 claims description 24
125000003118 aryl group Chemical group 0.000 claims description 24
229910052760 oxygen Inorganic materials 0.000 claims description 24
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 22
229910052736 halogen Inorganic materials 0.000 claims description 22
150000002367 halogens Chemical class 0.000 claims description 22
125000003545 alkoxy group Chemical group 0.000 claims description 21
125000003342 alkenyl group Chemical group 0.000 claims description 18
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 17
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
229910052717 sulfur Inorganic materials 0.000 claims description 14
125000004093 cyano group Chemical group *C#N 0.000 claims description 13
125000000753 cycloalkyl group Chemical group 0.000 claims description 13
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
125000005842 heteroatom Chemical group 0.000 claims description 11
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 10
125000001072 heteroaryl group Chemical group 0.000 claims description 8
201000001320 Atherosclerosis Diseases 0.000 claims description 7
125000000392 cycloalkenyl group Chemical group 0.000 claims description 7
125000001188 haloalkyl group Chemical group 0.000 claims description 7
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 7
125000002993 cycloalkylene group Chemical group 0.000 claims description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
239000000546 pharmaceutical excipient Substances 0.000 claims description 6
125000003107 substituted aryl group Chemical group 0.000 claims description 6
101100082497 Oryza sativa subsp. japonica PCF3 gene Proteins 0.000 claims description 5
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 4
239000003085 diluting agent Substances 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
HQUHMUAHNKEKBE-UHFFFAOYSA-N 2-[2,5-dimethyl-4-[[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]acetic acid Chemical compound CC=1N=C(C=2C=CC(=CC=2)C(F)(F)F)SC=1CSC1=CC(C)=C(OCC(O)=O)C=C1C HQUHMUAHNKEKBE-UHFFFAOYSA-N 0.000 claims description 2
SXAOVCZJVBKWNV-UHFFFAOYSA-N 2-[2-methoxy-5-methyl-4-[[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(OC)=CC(SCC2=C(N=C(S2)C=2C=CC(=CC=2)C(F)(F)F)C)=C1C SXAOVCZJVBKWNV-UHFFFAOYSA-N 0.000 claims description 2
VNEQJQIWZLEZKJ-UHFFFAOYSA-N 2-[3-methoxy-4-[[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenyl]-2-methylpropanoic acid Chemical compound COC1=CC(C(C)(C)C(O)=O)=CC=C1SCC1=C(C)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 VNEQJQIWZLEZKJ-UHFFFAOYSA-N 0.000 claims description 2
RICOCBHLOVJGHX-UHFFFAOYSA-N 3-methyl-3-[4-[[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenyl]butanoic acid Chemical compound CC=1N=C(C=2C=CC(=CC=2)C(F)(F)F)SC=1CSC1=CC=C(C(C)(C)CC(O)=O)C=C1 RICOCBHLOVJGHX-UHFFFAOYSA-N 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
239000008194 pharmaceutical composition Substances 0.000 claims description 2
SMLLFAYWFOGLIE-UHFFFAOYSA-N 2-[2-methyl-4-[[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]-2-phenylacetic acid Chemical compound CC=1N=C(C=2C=CC(=CC=2)C(F)(F)F)SC=1CSC(C=C1C)=CC=C1OC(C(O)=O)C1=CC=CC=C1 SMLLFAYWFOGLIE-UHFFFAOYSA-N 0.000 claims 1
DVWURGKSJLDMLH-UHFFFAOYSA-N 2-[5-(methoxymethyl)-2-methyl-4-[[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]acetic acid Chemical compound COCC1=CC(OCC(O)=O)=C(C)C=C1SCC1=C(C)N=C(C=2C=CC(=CC=2)C(F)(F)F)S1 DVWURGKSJLDMLH-UHFFFAOYSA-N 0.000 claims 1
FYWUOWGVPTVJNV-UHFFFAOYSA-N 2-[5-methyl-4-[[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2-propan-2-ylphenoxy]acetic acid Chemical compound C1=C(OCC(O)=O)C(C(C)C)=CC(SCC2=C(N=C(S2)C=2C=CC(=CC=2)C(F)(F)F)C)=C1C FYWUOWGVPTVJNV-UHFFFAOYSA-N 0.000 claims 1
YPGCWEMNNLXISK-UHFFFAOYSA-N hydratropic acid Chemical compound OC(=O)C(C)C1=CC=CC=C1 YPGCWEMNNLXISK-UHFFFAOYSA-N 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
239000000203 mixture Substances 0.000 abstract description 56
239000003814 drug Substances 0.000 abstract description 5
229940124597 therapeutic agent Drugs 0.000 abstract description 2
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 115
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 95
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 91
235000019439 ethyl acetate Nutrition 0.000 description 53
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 48
229960000583 acetic acid Drugs 0.000 description 43
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 38
239000000243 solution Substances 0.000 description 38
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 36
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HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 20
230000015572 biosynthetic process Effects 0.000 description 19
238000003818 flash chromatography Methods 0.000 description 19
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
238000000746 purification Methods 0.000 description 18
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238000003786 synthesis reaction Methods 0.000 description 18
229940095574 propionic acid Drugs 0.000 description 17
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
239000010410 layer Substances 0.000 description 16
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
150000004702 methyl esters Chemical class 0.000 description 14
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JQVJAQPUFIIRJP-UHFFFAOYSA-N 5-(chloromethyl)-4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole Chemical compound S1C(CCl)=C(C)N=C1C1=CC=C(C(F)(F)F)C=C1 JQVJAQPUFIIRJP-UHFFFAOYSA-N 0.000 description 13
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 13
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
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GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 9
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125000005309 thioalkoxy group Chemical group 0.000 description 7
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Classifications

- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- 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
- 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
- C07D277/26—Radicals substituted by sulfur atoms

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Diabetes (AREA)
Pharmacology & Pharmacy (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Obesity (AREA)
Hematology (AREA)
Heart & Thoracic Surgery (AREA)
Urology & Nephrology (AREA)
Vascular Medicine (AREA)
Cardiology (AREA)
Child & Adolescent Psychology (AREA)
Emergency Medicine (AREA)
Endocrinology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Thiazole And Isothizaole Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Medicinal Preparation (AREA)
Steroid Compounds (AREA)

OA1200400232A 2002-03-07 2003-02-24 Thiazole and oxazole derivatives which modulate PPAR activity. OA12780A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US36240202P	2002-03-07	2002-03-07

Publications (1)

Publication Number	Publication Date
OA12780A true OA12780A (en)	2006-07-07

Family

ID=27789157

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Application Number	Title	Priority Date	Filing Date
OA1200400232A OA12780A (en)	2002-03-07	2003-02-24	Thiazole and oxazole derivatives which modulate PPAR activity.

Country Status (29)

Country	Link
US (1)	US20030207924A1 (de)
EP (1)	EP1482935B1 (de)
JP (1)	JP2005528348A (de)
KR (1)	KR20040091693A (de)
AP (1)	AP2004003124A0 (de)
AR (1)	AR038881A1 (de)
AT (1)	ATE405260T1 (de)
AU (1)	AU2003206059A1 (de)
BR (1)	BR0308277A (de)
CA (1)	CA2478520A1 (de)
CO (1)	CO5601012A2 (de)
DE (1)	DE60323060D1 (de)
EA (1)	EA200400943A1 (de)
EC (1)	ECSP045285A (de)
ES (1)	ES2310650T3 (de)
HN (1)	HN2003000090A (de)
IS (1)	IS7377A (de)
MA (1)	MA27181A1 (de)
MX (1)	MXPA04007564A (de)
NO (1)	NO20044242L (de)
OA (1)	OA12780A (de)
PA (1)	PA8567801A1 (de)
PE (1)	PE20030989A1 (de)
PL (1)	PL372969A1 (de)
TN (1)	TNSN04168A1 (de)
TW (1)	TW200305403A (de)
UY (1)	UY27695A1 (de)
WO (1)	WO2003074050A1 (de)
ZA (1)	ZA200406068B (de)

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CA2662305C (en)	2006-09-07	2012-04-17	Amgen Inc.	Heterocyclic gpr40 modulators
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ES2446419T3 (es)	2007-04-16	2014-03-07	Amgen, Inc	Moduladores de GPR40 de ácidos bifenilfenoxi, tiofenil y aminofenilpropanoico sustituidos
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2002
- 2002-12-20 US US10/324,148 patent/US20030207924A1/en not_active Abandoned
2003
- 2003-02-24 JP JP2003572567A patent/JP2005528348A/ja not_active Abandoned
- 2003-02-24 AU AU2003206059A patent/AU2003206059A1/en not_active Abandoned
- 2003-02-24 CA CA002478520A patent/CA2478520A1/en not_active Abandoned
- 2003-02-24 EA EA200400943A patent/EA200400943A1/ru unknown
- 2003-02-24 MX MXPA04007564A patent/MXPA04007564A/es active IP Right Grant
- 2003-02-24 BR BR0308277-6A patent/BR0308277A/pt not_active IP Right Cessation
- 2003-02-24 OA OA1200400232A patent/OA12780A/en unknown
- 2003-02-24 PL PL03372969A patent/PL372969A1/xx not_active Application Discontinuation
- 2003-02-24 AP APAP/P/2004/003124A patent/AP2004003124A0/en unknown
- 2003-02-24 EP EP03702943A patent/EP1482935B1/de not_active Expired - Lifetime
- 2003-02-24 DE DE60323060T patent/DE60323060D1/de not_active Expired - Fee Related
- 2003-02-24 KR KR10-2004-7013951A patent/KR20040091693A/ko not_active Ceased
- 2003-02-24 WO PCT/IB2003/000708 patent/WO2003074050A1/en not_active Ceased
- 2003-02-24 ES ES03702943T patent/ES2310650T3/es not_active Expired - Lifetime
- 2003-02-24 AT AT03702943T patent/ATE405260T1/de not_active IP Right Cessation
- 2003-02-27 PA PA20038567801A patent/PA8567801A1/es unknown
- 2003-03-04 PE PE2003000210A patent/PE20030989A1/es not_active Application Discontinuation
- 2003-03-05 AR ARP030100737A patent/AR038881A1/es unknown
- 2003-03-06 UY UY27695A patent/UY27695A1/es not_active Application Discontinuation
- 2003-03-06 TW TW092104790A patent/TW200305403A/zh unknown
- 2003-03-06 HN HN2003000090A patent/HN2003000090A/es unknown
2004
- 2004-07-29 ZA ZA200406068A patent/ZA200406068B/en unknown
- 2004-07-29 IS IS7377A patent/IS7377A/is unknown
- 2004-08-24 CO CO04082302A patent/CO5601012A2/es not_active Application Discontinuation
- 2004-08-30 MA MA27839A patent/MA27181A1/fr unknown
- 2004-09-03 TN TNP2004000168A patent/TNSN04168A1/fr unknown
- 2004-09-07 EC EC2004005285A patent/ECSP045285A/es unknown
- 2004-10-06 NO NO20044242A patent/NO20044242L/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
MXPA04007564A (es)	2004-11-10
CO5601012A2 (es)	2006-01-31
ECSP045285A (es)	2004-10-26
KR20040091693A (ko)	2004-10-28
CA2478520A1 (en)	2003-09-12
MA27181A1 (fr)	2005-01-03
US20030207924A1 (en)	2003-11-06
ATE405260T1 (de)	2008-09-15
NO20044242L (no)	2004-10-06
IS7377A (is)	2004-07-29
EP1482935B1 (de)	2008-08-20
AR038881A1 (es)	2005-02-02
JP2005528348A (ja)	2005-09-22
PA8567801A1 (es)	2003-11-12
AP2004003124A0 (en)	2004-09-30
ES2310650T3 (es)	2009-01-16
AU2003206059A1 (en)	2003-09-16
UY27695A1 (es)	2003-10-31
TW200305403A (en)	2003-11-01
PE20030989A1 (es)	2003-11-29
PL372969A1 (en)	2005-08-08
EP1482935A1 (de)	2004-12-08
WO2003074050A1 (en)	2003-09-12
BR0308277A (pt)	2004-12-28
ZA200406068B (en)	2005-09-06
HN2003000090A (es)	2004-05-05
TNSN04168A1 (fr)	2007-03-12
DE60323060D1 (de)	2008-10-02
EA200400943A1 (ru)	2005-02-24

Publication	Publication Date	Title
EP1482935B1 (de)	2008-08-20	Thiazol- und oxazolderivaten als ppar modulatoren
US6833380B2 (en)	2004-12-21	Compounds that modulate PPAR activity and methods of preparation
US7109222B2 (en)	2006-09-19	Compounds that modulate PPAR activity and methods of preparation
AU758758B2 (en)	2003-03-27	Substituted oxazoles and thiazoles derivatives as HPPAR alpha activators
CN101384568B (zh)	2012-12-12	乙酰辅酶a羧化酶(acc)抑制剂及其在糖尿病、肥胖症和代谢综合征中的应用
RS82904A (sr)	2007-02-05	Jedinjenja koja moduliraju delovanje ppar i postupci za njihovo dobijanje
CA2377126C (en)	2009-01-27	Thiazole and oxazole derivatives and their pharmaceutical use
WO2011078370A1 (ja)	2011-06-30	新規パラバン酸誘導体及びそれらを有効成分とする医薬
JPH06779B2 (ja)	1994-01-05	チアゾリジオン誘導体およびそれを含んでなる医薬組成物
CZ176393A3 (en)	1994-04-13	Oxazolidine derivatives, process of their preparation and pharmaceutical preparations in which they are comprised
WO2009109998A1 (en)	2009-09-11	Novel protein tyrosine phosphatase - ib inhibitors
CA2626483A1 (en)	2007-05-18	Compounds and compositions as ppar modulators
MXPA04007177A (es)	2004-10-29	Alimentacion para animales baja en fosforo y metodo para hacer la misma.
US2971021A (en)	1961-02-07	1-amino-1-carboalkoxycyclohexanes
WO1992021666A1 (fr)	1992-12-10	Derives de thiazole antagonistes de recepteurs a l'angiotensine ii
JP3836521B2 (ja)	2006-10-25	２，４−チアゾリジンジオン誘導体、その製造法およびそれを含んでなる医薬組成物