OA12781A - Thiazole and oxazole derivatives that modulate PPAR activity. - Google Patents

Thiazole and oxazole derivatives that modulate PPAR activity. Download PDF

Info

Publication number: OA12781A
Authority: OA; OAPI
Prior art keywords: methyl; phenyl; yloxy; thiazol; acetic acid
Prior art date: 2002-03-07

Application number

OA1200400233A

Other languages

English (en)

Inventor

Xue-Min Cheng

Noe Ouano Erasga

Gary Frderick Filzen

Andrew George Geyer

Chitase Lee

Bharatu 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

2003-03-03

Publication date

2006-07-07

2003-03-03 Application filed by Warner Lambert Co filed Critical Warner Lambert Co

2006-07-07 Publication of OA12781A publication Critical patent/OA12781A/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
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 title description 2
150000007978 oxazole derivatives Chemical class 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 195
238000000034 method Methods 0.000 claims abstract description 22
208000031226 Hyperlipidaemia Diseases 0.000 claims abstract description 14
150000003839 salts Chemical class 0.000 claims abstract description 12
208000035150 Hypercholesterolemia Diseases 0.000 claims abstract description 11
241000124008 Mammalia Species 0.000 claims abstract description 9
-1 -(CH2)raNR6R7 Proteins 0.000 claims description 92
125000000217 alkyl group Chemical group 0.000 claims description 78
229910052739 hydrogen Inorganic materials 0.000 claims description 46
239000001257 hydrogen Substances 0.000 claims description 46
125000005842 heteroatom Chemical group 0.000 claims description 41
229910052760 oxygen Inorganic materials 0.000 claims description 40
125000003118 aryl group Chemical group 0.000 claims description 37
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 32
125000000304 alkynyl group Chemical group 0.000 claims description 32
229910052717 sulfur Inorganic materials 0.000 claims description 30
125000003545 alkoxy group Chemical group 0.000 claims description 29
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 28
125000003342 alkenyl group Chemical group 0.000 claims description 25
125000004429 atom Chemical group 0.000 claims description 24
229910052799 carbon Inorganic materials 0.000 claims description 22
125000004432 carbon atom Chemical group C* 0.000 claims description 20
229910052736 halogen Inorganic materials 0.000 claims description 20
150000002367 halogens Chemical class 0.000 claims description 20
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 17
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
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 15
125000004093 cyano group Chemical group *C#N 0.000 claims description 15
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125000001424 substituent group Chemical group 0.000 claims description 15
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125000006588 heterocycloalkylene group Chemical group 0.000 claims description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
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VTGKVTQZAONBPL-UHFFFAOYSA-N 2-[8-[[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-4-oxochromen-5-yl]oxyacetic acid Chemical compound S1C(CSC=2C3=C(C(C=CO3)=O)C(OCC(O)=O)=CC=2)=C(C)N=C1C1=CC=C(C(F)(F)F)C=C1 VTGKVTQZAONBPL-UHFFFAOYSA-N 0.000 claims description 2
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DAAMIPJNRSFJBV-UHFFFAOYSA-N 2-[[4-[[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-6-oxo-7,8-dihydro-5h-naphthalen-1-yl]oxy]acetic acid Chemical compound S1C(CSC=2C=3CC(=O)CCC=3C(OCC(O)=O)=CC=2)=C(C)N=C1C1=CC=C(C(F)(F)F)C=C1 DAAMIPJNRSFJBV-UHFFFAOYSA-N 0.000 claims description 2
XJXJPQWJBAPENY-UHFFFAOYSA-N 2-[[4-[[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-7-oxo-6,8-dihydro-5h-naphthalen-1-yl]oxy]acetic acid Chemical compound S1C(CSC=2C=3CCC(=O)CC=3C(OCC(O)=O)=CC=2)=C(C)N=C1C1=CC=C(C(F)(F)F)C=C1 XJXJPQWJBAPENY-UHFFFAOYSA-N 0.000 claims description 2
IOCWGZNOOXOJDZ-UHFFFAOYSA-N 2-[[5-[[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-4-oxo-2,3-dihydrochromen-8-yl]oxy]acetic acid Chemical compound S1C(CSC=2C=3C(=O)CCOC=3C(OCC(O)=O)=CC=2)=C(C)N=C1C1=CC=C(C(F)(F)F)C=C1 IOCWGZNOOXOJDZ-UHFFFAOYSA-N 0.000 claims description 2
WSXPAZMHQPPIOW-UHFFFAOYSA-N 2-[[5-methyl-7-[[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-2,3-dihydro-1h-inden-4-yl]oxy]acetic acid Chemical compound S1C(CSC=2C=3CCCC=3C(OCC(O)=O)=C(C)C=2)=C(C)N=C1C1=CC=C(C(F)(F)F)C=C1 WSXPAZMHQPPIOW-UHFFFAOYSA-N 0.000 claims description 2
FJTRLFAKDFQDSC-UHFFFAOYSA-N 2-[[7-[[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]-1-benzofuran-4-yl]oxy]acetic acid Chemical compound S1C(CSC=2C=3OC=CC=3C(OCC(O)=O)=CC=2)=C(C)N=C1C1=CC=C(C(F)(F)F)C=C1 FJTRLFAKDFQDSC-UHFFFAOYSA-N 0.000 claims description 2
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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
- A61P3/06—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
- 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
- C07D277/26—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)
Diabetes (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Obesity (AREA)
Hematology (AREA)
Cardiology (AREA)
Urology & Nephrology (AREA)
Vascular Medicine (AREA)
Heart & Thoracic Surgery (AREA)
Emergency Medicine (AREA)
Endocrinology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Thiazole And Isothizaole Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
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OA1200400233A 2002-03-07 2003-03-03 Thiazole and oxazole derivatives that modulate PPAR activity. OA12781A (en)

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US36240002P	2002-03-07	2002-03-07

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EP (1)	EP1485091A1 (es)
JP (1)	JP2005524665A (es)
KR (1)	KR20040091694A (es)
CN (1)	CN1638768A (es)
AP (1)	AP2004003123A0 (es)
AR (1)	AR038883A1 (es)
AU (1)	AU2003207891A1 (es)
BR (1)	BR0308221A (es)
CA (1)	CA2476580A1 (es)
CO (1)	CO5601013A2 (es)
EA (1)	EA200401160A1 (es)
EC (1)	ECSP045275A (es)
GT (1)	GT200300053A (es)
HR (1)	HRP20040810A2 (es)
IL (1)	IL163768A0 (es)
IS (1)	IS7399A (es)
MA (1)	MA27182A1 (es)
MX (1)	MXPA04008624A (es)
NO (1)	NO20044245L (es)
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PA (1)	PA8568701A1 (es)
PE (1)	PE20031010A1 (es)
PL (1)	PL372971A1 (es)
TN (1)	TNSN04167A1 (es)
TW (1)	TW200400027A (es)
UY (1)	UY27704A1 (es)
WO (1)	WO2003074052A1 (es)
ZA (1)	ZA200406491B (es)

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Publication number	Publication date
MXPA04008624A (es)	2004-12-06
EA200401160A1 (ru)	2005-02-24
NO20044245L (no)	2004-10-06
AP2004003123A0 (en)	2004-09-30
AU2003207891A1 (en)	2003-09-16
US6833380B2 (en)	2004-12-21
AR038883A1 (es)	2005-02-02
IS7399A (is)	2004-08-12
GT200300053A (es)	2003-10-10
EP1485091A1 (en)	2004-12-15
ECSP045275A (es)	2004-10-26
TNSN04167A1 (fr)	2007-03-12
ZA200406491B (en)	2006-05-31
CO5601013A2 (es)	2006-01-31
PL372971A1 (en)	2005-08-08
PE20031010A1 (es)	2003-12-12
US20030207916A1 (en)	2003-11-06
CN1638768A (zh)	2005-07-13
MA27182A1 (fr)	2005-01-03
KR20040091694A (ko)	2004-10-28
WO2003074052A1 (en)	2003-09-12
JP2005524665A (ja)	2005-08-18
BR0308221A (pt)	2005-01-04
HRP20040810A2 (en)	2004-12-31
CA2476580A1 (en)	2003-09-12
PA8568701A1 (es)	2003-11-12
IL163768A0 (en)	2005-12-18
TW200400027A (en)	2004-01-01
UY27704A1 (es)	2003-10-31

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WO2006117743A1 (en)	2006-11-09	Substituted aromatic compounds as antidiabetic agents
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