ZA200501097B - Novel 2-arylthiazole compounds as PPARALPHA and PPARGAMA agonists - Google Patents

Novel 2-arylthiazole compounds as PPARALPHA and PPARGAMA agonists Download PDF

Info

Publication number: ZA200501097B
Authority: ZA; South Africa
Prior art keywords: phenyl; ethoxy; methyl; thiazol; propionic acid
Prior art date: 2002-08-30

Application number

ZA200501097A

Other languages

English (en)

Inventor

Binggeli Alfred

Grether Uwe

Hilpert Hans

Hirth Georges

Maerki Hans-Peter

Peter Markus Mohr Meyer

Original Assignee

Hoffmann La Roche

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.)

2002-08-30

Filing date

2005-02-07

Publication date

2006-11-29

2005-02-07 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

2006-11-29 Publication of ZA200501097B publication Critical patent/ZA200501097B/en

Links

150000001875 compounds Chemical class 0.000 title claims description 117
239000000556 agonist Substances 0.000 title claims description 14
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 108
239000001257 hydrogen Substances 0.000 claims description 60
229910052739 hydrogen Inorganic materials 0.000 claims description 60
238000000034 method Methods 0.000 claims description 38
239000000203 mixture Substances 0.000 claims description 33
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 32
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 27
201000010099 disease Diseases 0.000 claims description 26
150000002431 hydrogen Chemical class 0.000 claims description 25
-1 lower-alkenyl Chemical class 0.000 claims description 23
125000004432 carbon atom Chemical group C* 0.000 claims description 22
235000019260 propionic acid Nutrition 0.000 claims description 22
208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 22
150000002148 esters Chemical class 0.000 claims description 21
238000011282 treatment Methods 0.000 claims description 20
150000003839 salts Chemical class 0.000 claims description 19
229910052736 halogen Inorganic materials 0.000 claims description 17
150000002367 halogens Chemical class 0.000 claims description 17
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims description 16
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
206010012601 diabetes mellitus Diseases 0.000 claims description 11
125000006239 protecting group Chemical group 0.000 claims description 11
125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 10
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125000003118 aryl group Chemical group 0.000 claims description 9
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230000008694 endothelial dysfunction Effects 0.000 claims description 8
125000001072 heteroaryl group Chemical group 0.000 claims description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
208000001145 Metabolic Syndrome Diseases 0.000 claims description 7
101150014691 PPARA gene Proteins 0.000 claims description 7
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230000002062 proliferating effect Effects 0.000 claims description 7
125000000753 cycloalkyl group Chemical group 0.000 claims description 6
230000001225 therapeutic effect Effects 0.000 claims description 6
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 5
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239000013543 active substance Substances 0.000 claims description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 4
OTUKSARQRIIQDU-UHFFFAOYSA-N 3-[4-[[2-(4-chlorophenyl)-1,3-thiazol-4-yl]methoxy]-2-methylphenyl]-2-ethoxypropanoic acid Chemical compound C1=C(C)C(CC(OCC)C(O)=O)=CC=C1OCC1=CSC(C=2C=CC(Cl)=CC=2)=N1 OTUKSARQRIIQDU-UHFFFAOYSA-N 0.000 claims description 3
125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
241001465754 Metazoa Species 0.000 claims description 3
125000001424 substituent group Chemical group 0.000 claims description 3
DSOBEFZGPISYQH-UHFFFAOYSA-N 2-[[4-[cyclopropyl-[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methoxy]-2-methylphenyl]methyl]butanoic acid Chemical compound C1=C(C)C(CC(CC)C(O)=O)=CC=C1OC(C1=C(N=C(S1)C=1C=CC(=CC=1)C(F)(F)F)C)C1CC1 DSOBEFZGPISYQH-UHFFFAOYSA-N 0.000 claims description 2
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150000002989 phenols Chemical class 0.000 description 5
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- 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
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- 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

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Gastroenterology & Hepatology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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ZA200501097A 2002-08-30 2005-02-07 Novel 2-arylthiazole compounds as PPARALPHA and PPARGAMA agonists ZA200501097B (en)

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Application Number	Priority Date	Filing Date	Title
EP02019146		2002-08-30

Publications (1)

Publication Number	Publication Date
ZA200501097B true ZA200501097B (en)	2006-11-29

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ZA200501097A ZA200501097B (en)	2002-08-30	2005-02-07	Novel 2-arylthiazole compounds as PPARALPHA and PPARGAMA agonists

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US (1)	US6809110B2 (zh)
EP (1)	EP1537091B1 (zh)
JP (2)	JP4533141B2 (zh)
KR (1)	KR100736955B1 (zh)
CN (1)	CN100475810C (zh)
AR (1)	AR041079A1 (zh)
AT (1)	ATE483699T1 (zh)
BR (1)	BR0313946A (zh)
CA (1)	CA2495942C (zh)
DE (1)	DE60334461D1 (zh)
DK (1)	DK1537091T3 (zh)
ES (1)	ES2350340T3 (zh)
GT (1)	GT200300183A (zh)
HK (1)	HK1082504A1 (zh)
HR (1)	HRP20050158A2 (zh)
IL (1)	IL166833A (zh)
MX (1)	MXPA05002115A (zh)
MY (1)	MY141020A (zh)
NO (1)	NO329777B1 (zh)
NZ (1)	NZ537897A (zh)
PA (1)	PA8581201A1 (zh)
PE (1)	PE20040982A1 (zh)
PL (1)	PL375779A1 (zh)
PT (1)	PT1537091E (zh)
RU (1)	RU2296754C2 (zh)
SI (1)	SI1537091T1 (zh)
TW (1)	TWI338686B (zh)
UY (1)	UY27959A1 (zh)
WO (1)	WO2004020420A1 (zh)
ZA (1)	ZA200501097B (zh)

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JP2009084156A (ja) *	2006-01-18	2009-04-23	Nissan Chem Ind Ltd	チアゾール置換アセトニトリルの製造方法
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KR20080082541A (ko) *	2007-03-07	2008-09-11	동아제약주식회사	퍼옥시좀 증식자-활성화 감마 수용체를 조절하는 신규한페닐프로판산 유도체의 제조방법 및 약학적 용도
DE102007038251A1 (de) *	2007-08-13	2009-02-19	Boehringer Ingelheim Pharma Gmbh & Co. Kg	Neues Herstellverfahren
CN101928259B (zh) *	2009-06-18	2012-10-03	南京海辰药业有限公司	2-芳基噻唑衍生物及其药物组合物
CN102285933B (zh) *	2010-06-18	2016-03-09	浙江海正药业股份有限公司	一种对亚型过氧化物酶增殖物激活受体具有激动作用的化合物、其制备方法和应用
CN102351852B (zh) *	2011-08-23	2014-06-18	上海交通大学	苯并呋喃类化合物及其制备方法、用途
EP2758041B1 (de)	2011-09-20	2021-01-13	Basf Se	Niedermolekulare modulatoren des kälte-menthol-rezeptors trpm8 und deren verwendung
EP3478297A1 (en)	2016-06-30	2019-05-08	INSERM (Institut National de la Santé et de la Recherche Médicale)	Methods and pharmaceutical compositions for the treatment of cardiomyopathies
CA3054452A1 (en) *	2017-03-14	2018-09-20	Dana-Farber Cancer Institute, Inc.	Small molecule sensitization of bax activation for induction of cell death
WO2020201263A1 (en)	2019-04-01	2020-10-08	INSERM (Institut National de la Santé et de la Recherche Médicale)	Methods and pharmaceutical compositions for the treatment and prevention of cardiac remodeling
CN115894379A (zh) *	2022-01-20	2023-04-04	中国药科大学	海因类化合物及其医药用途

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WO2004020420A1 (en) *	2002-08-30	2004-03-11	F.Hoffmann-La Roche Ag	Novel 2-arylthiazole compounds as pparalpha and ppargama agonists

2003
- 2003-08-21 WO PCT/EP2003/009281 patent/WO2004020420A1/en active IP Right Grant
- 2003-08-21 SI SI200331904T patent/SI1537091T1/sl unknown
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- 2003-08-21 DK DK03757762.4T patent/DK1537091T3/da active
- 2003-08-21 RU RU2005109163/04A patent/RU2296754C2/ru not_active IP Right Cessation
- 2003-08-21 EP EP03757762A patent/EP1537091B1/en not_active Expired - Lifetime
- 2003-08-21 DE DE60334461T patent/DE60334461D1/de not_active Expired - Lifetime
- 2003-08-21 BR BR0313946-8A patent/BR0313946A/pt not_active IP Right Cessation
- 2003-08-21 CN CNB038205432A patent/CN100475810C/zh not_active Expired - Fee Related
- 2003-08-21 PT PT03757762T patent/PT1537091E/pt unknown
- 2003-08-21 ES ES03757762T patent/ES2350340T3/es not_active Expired - Lifetime
- 2003-08-26 PA PA20038581201A patent/PA8581201A1/es unknown
- 2003-08-26 TW TW092123445A patent/TWI338686B/zh not_active IP Right Cessation
- 2003-08-26 PE PE2003000873A patent/PE20040982A1/es not_active Application Discontinuation
- 2003-08-27 UY UY27959A patent/UY27959A1/es not_active Application Discontinuation
- 2003-08-27 GT GT200300183A patent/GT200300183A/es unknown
- 2003-08-28 MY MYPI20033266A patent/MY141020A/en unknown
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- 2003-08-28 US US10/650,434 patent/US6809110B2/en not_active Expired - Fee Related
2005
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2006
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2010
- 2010-01-14 JP JP2010006072A patent/JP2010132671A/ja active Pending

Also Published As

Publication number	Publication date
KR20050057083A (ko)	2005-06-16
HK1082504A1 (en)	2006-06-09
DE60334461D1 (de)	2010-11-18
MY141020A (en)	2010-02-25
PE20040982A1 (es)	2004-12-30
TWI338686B (en)	2011-03-11
NZ537897A (en)	2007-08-31
MXPA05002115A (es)	2005-05-23
BR0313946A (pt)	2005-07-12
ES2350340T3 (es)	2011-01-21
CN100475810C (zh)	2009-04-08
WO2004020420A1 (en)	2004-03-11
GT200300183A (es)	2004-04-15
CN1678596A (zh)	2005-10-05
PA8581201A1 (es)	2004-09-16
AR041079A1 (es)	2005-04-27
AU2003273801A1 (en)	2004-03-19
JP2010132671A (ja)	2010-06-17
US20040110807A1 (en)	2004-06-10
TW200407133A (en)	2004-05-16
PT1537091E (pt)	2010-11-11
SI1537091T1 (sl)	2010-12-31
KR100736955B1 (ko)	2007-07-09
DK1537091T3 (da)	2010-11-08
JP4533141B2 (ja)	2010-09-01
HRP20050158A2 (en)	2006-11-30
NO329777B1 (no)	2010-12-13
JP2006502151A (ja)	2006-01-19
US6809110B2 (en)	2004-10-26
CA2495942C (en)	2010-03-23
IL166833A (en)	2010-12-30
RU2005109163A (ru)	2006-01-20
UY27959A1 (es)	2004-02-27
RU2296754C2 (ru)	2007-04-10
EP1537091B1 (en)	2010-10-06
EP1537091A1 (en)	2005-06-08
PL375779A1 (en)	2005-12-12
CA2495942A1 (en)	2004-03-11
NO20050620L (no)	2005-03-03
ATE483699T1 (de)	2010-10-15

Publication	Publication Date	Title
ZA200501097B (en)	2006-11-29	Novel 2-arylthiazole compounds as PPARALPHA and PPARGAMA agonists
EP1572203B1 (en)	2007-11-07	Substituted 4-alkoxyoxazol derivatives as ppar agonists
AU2002342244B2 (en)	2005-06-16	Carboxylic acid substituted oxazole derivatives for use as PPAR-alpha and -gamma activators in the treatment of diabetes
US7897815B2 (en)	2011-03-01	Hexafluoroisopropanol derivatives
WO2006037480A1 (en)	2006-04-13	Hexafluoroisopropanol substituted ether derivatives
CA2499721C (en)	2011-03-15	Chirale oxazole-arylpropionic acid derivatives and their use as ppar agonists
AU2003273801B2 (en)	2007-02-22	Novel 2-arylthiazole compounds as Pparalpha and Ppargama agonists