JP2004506721A5 - - Google Patents
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- Publication number
- JP2004506721A5 JP2004506721A5 JP2002521432A JP2002521432A JP2004506721A5 JP 2004506721 A5 JP2004506721 A5 JP 2004506721A5 JP 2002521432 A JP2002521432 A JP 2002521432A JP 2002521432 A JP2002521432 A JP 2002521432A JP 2004506721 A5 JP2004506721 A5 JP 2004506721A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- phenyl
- alkyl
- compound
- ethoxy
- Prior art date
- Legal status (The legal status 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 status listed.)
- Withdrawn
Links
- 150000001875 compounds Chemical class 0.000 description 40
- -1 thiophen-2,5-diyl Chemical group 0.000 description 28
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 19
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 14
- 150000003839 salts Chemical class 0.000 description 14
- 239000012453 solvate Substances 0.000 description 13
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 10
- 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 description 10
- 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 description 10
- 241000124008 Mammalia Species 0.000 description 9
- 125000001475 halogen functional group Chemical group 0.000 description 9
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 description 8
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 8
- 150000004677 hydrates Chemical class 0.000 description 8
- 125000001544 thienyl group Chemical group 0.000 description 8
- 125000001624 naphthyl group Chemical group 0.000 description 6
- 125000005493 quinolyl group Chemical group 0.000 description 6
- 102000005962 receptors Human genes 0.000 description 5
- 108020003175 receptors Proteins 0.000 description 5
- 125000004103 aminoalkyl group Chemical group 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 125000001072 heteroaryl group Chemical group 0.000 description 3
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 3
- 210000002966 serum Anatomy 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- UYZRCSAVQYPXAQ-UHFFFAOYSA-N 2-methyl-3-[4-[2-[5-methyl-2-(1-methylcyclohexyl)-1,3-oxazol-4-yl]ethoxy]phenyl]-2-(2-methylphenoxy)propanoic acid Chemical compound CC=1OC(C2(C)CCCCC2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)OC1=CC=CC=C1C UYZRCSAVQYPXAQ-UHFFFAOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- 102000015779 HDL Lipoproteins Human genes 0.000 description 2
- 108010010234 HDL Lipoproteins Proteins 0.000 description 2
- 102000007330 LDL Lipoproteins Human genes 0.000 description 2
- 108010007622 LDL Lipoproteins Proteins 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 150000003626 triacylglycerols Chemical class 0.000 description 2
- KWSPYUOBNIMILB-SANMLTNESA-N (2s)-2-methyl-3-[4-[2-(5-methyl-2-thiophen-2-yl-1,3-oxazol-4-yl)ethoxy]phenyl]-2-phenoxypropanoic acid Chemical compound O([C@@](C)(CC1=CC=C(C=C1)OCCC=1N=C(OC=1C)C=1SC=CC=1)C(O)=O)C1=CC=CC=C1 KWSPYUOBNIMILB-SANMLTNESA-N 0.000 description 1
- GGVARJZTVCDHIS-SANMLTNESA-N (2s)-3-[4-[2-(2-cyclohexyl-5-methyl-1,3-oxazol-4-yl)ethoxy]phenyl]-2-(4-methylphenoxy)propanoic acid Chemical compound O([C@@H](CC1=CC=C(C=C1)OCCC=1N=C(OC=1C)C1CCCCC1)C(O)=O)C1=CC=C(C)C=C1 GGVARJZTVCDHIS-SANMLTNESA-N 0.000 description 1
- VITUOJRLJBPZMW-UHFFFAOYSA-N 2-(2-methoxyphenoxy)-2-methyl-3-[4-[2-(5-methyl-2-thiophen-2-yl-1,3-oxazol-4-yl)ethoxy]phenyl]propanoic acid Chemical compound COC1=CC=CC=C1OC(C)(C(O)=O)CC(C=C1)=CC=C1OCCC1=C(C)OC(C=2SC=CC=2)=N1 VITUOJRLJBPZMW-UHFFFAOYSA-N 0.000 description 1
- QYHAWNLDQLOSNT-UHFFFAOYSA-N 2-(3-chlorophenoxy)-3-[4-[2-(2-cyclohexyl-5-methyl-1,3-oxazol-4-yl)ethoxy]phenyl]-2-methylpropanoic acid Chemical compound CC=1OC(C2CCCCC2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)OC1=CC=CC(Cl)=C1 QYHAWNLDQLOSNT-UHFFFAOYSA-N 0.000 description 1
- GYDYGMALAVXYJR-UHFFFAOYSA-N 2-methyl-2-(2-methylphenoxy)-3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]propanoic acid Chemical compound CC=1OC(C=2C=CC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)OC1=CC=CC=C1C GYDYGMALAVXYJR-UHFFFAOYSA-N 0.000 description 1
- UGFDMEAQMIZMJH-UHFFFAOYSA-N 2-methyl-2-(2-methylphenoxy)-3-[4-[2-(5-methyl-2-thiophen-2-yl-1,3-oxazol-4-yl)ethoxy]phenyl]propanoic acid Chemical compound CC=1OC(C=2SC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)OC1=CC=CC=C1C UGFDMEAQMIZMJH-UHFFFAOYSA-N 0.000 description 1
- JSTSZHVRXHMZQK-UHFFFAOYSA-N 2-methyl-3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]-2-phenoxypropanoic acid Chemical compound CC=1OC(C=2C=CC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)OC1=CC=CC=C1 JSTSZHVRXHMZQK-UHFFFAOYSA-N 0.000 description 1
- XNNSVDBLAAWIHF-UHFFFAOYSA-N 2-methyl-3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]-2-quinolin-6-yloxypropanoic acid Chemical compound N=1C(CCOC=2C=CC(CC(C)(OC=3C=C4C=CC=NC4=CC=3)C(O)=O)=CC=2)=C(C)OC=1C1=CC=CC=C1 XNNSVDBLAAWIHF-UHFFFAOYSA-N 0.000 description 1
- KWSPYUOBNIMILB-UHFFFAOYSA-N 2-methyl-3-[4-[2-(5-methyl-2-thiophen-2-yl-1,3-oxazol-4-yl)ethoxy]phenyl]-2-phenoxypropanoic acid Chemical compound CC=1OC(C=2SC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)OC1=CC=CC=C1 KWSPYUOBNIMILB-UHFFFAOYSA-N 0.000 description 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- KLYSGRRZNYRRDA-UHFFFAOYSA-N 3-[4-[2-(2-cyclohexyl-5-methyl-1,3-oxazol-4-yl)ethoxy]phenyl]-2-(2-methoxyphenoxy)-2-methylpropanoic acid Chemical compound COC1=CC=CC=C1OC(C)(C(O)=O)CC(C=C1)=CC=C1OCCC1=C(C)OC(C2CCCCC2)=N1 KLYSGRRZNYRRDA-UHFFFAOYSA-N 0.000 description 1
- GGVARJZTVCDHIS-UHFFFAOYSA-N 3-[4-[2-(2-cyclohexyl-5-methyl-1,3-oxazol-4-yl)ethoxy]phenyl]-2-(4-methylphenoxy)propanoic acid Chemical compound CC=1OC(C2CCCCC2)=NC=1CCOC(C=C1)=CC=C1CC(C(O)=O)OC1=CC=C(C)C=C1 GGVARJZTVCDHIS-UHFFFAOYSA-N 0.000 description 1
- ZJASNYLZHSZJRM-UHFFFAOYSA-N 3-[4-[2-(2-cyclohexyl-5-methyl-1,3-oxazol-4-yl)ethoxy]phenyl]-2-methyl-2-(2-methylphenoxy)propanoic acid Chemical compound CC=1OC(C2CCCCC2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)OC1=CC=CC=C1C ZJASNYLZHSZJRM-UHFFFAOYSA-N 0.000 description 1
- DVIHJHMWKIYVCZ-UHFFFAOYSA-N 3-[4-[2-(2-cyclohexyl-5-methyl-1,3-oxazol-4-yl)ethoxy]phenyl]-2-methyl-2-(3-thiophen-3-ylphenoxy)propanoic acid Chemical compound CC=1OC(C2CCCCC2)=NC=1CCOC(C=C1)=CC=C1CC(C)(C(O)=O)OC(C=1)=CC=CC=1C=1C=CSC=1 DVIHJHMWKIYVCZ-UHFFFAOYSA-N 0.000 description 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- JRQXNAQWKXCZLC-UHFFFAOYSA-N 5-methyl-2-thiophen-2-yl-1,3-oxazole Chemical compound O1C(C)=CN=C1C1=CC=CS1 JRQXNAQWKXCZLC-UHFFFAOYSA-N 0.000 description 1
- 0 CC(Cc(cc1)ccc1OCCc1c(C)[o]c(-c2ccccc2)n1)(C(O)=O)Oc1ccc(*)c(*)c1* Chemical compound CC(Cc(cc1)ccc1OCCc1c(C)[o]c(-c2ccccc2)n1)(C(O)=O)Oc1ccc(*)c(*)c1* 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 238000003745 diagnosis Methods 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US22723400P | 2000-08-23 | 2000-08-23 | |
| PCT/US2001/022616 WO2002016331A1 (en) | 2000-08-23 | 2001-08-23 | Oxazolyl-arylpropionic acid derivatives and their use as ppar agonists |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2004506721A JP2004506721A (ja) | 2004-03-04 |
| JP2004506721A5 true JP2004506721A5 (https=) | 2008-10-16 |
Family
ID=22852309
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002521432A Withdrawn JP2004506721A (ja) | 2000-08-23 | 2001-08-23 | オキサゾリル−アリールプロピオン酸誘導体およびそのｐｐａｒアゴニストとしての使用 |
Country Status (26)
| Country | Link |
|---|---|
| US (2) | US6930120B2 (https=) |
| EP (1) | EP1313716B1 (https=) |
| JP (1) | JP2004506721A (https=) |
| KR (1) | KR20030027054A (https=) |
| CN (1) | CN1471517A (https=) |
| AT (1) | ATE361283T1 (https=) |
| AU (1) | AU2001284659A1 (https=) |
| BR (1) | BR0113409A (https=) |
| CA (1) | CA2418104A1 (https=) |
| CY (1) | CY1107679T1 (https=) |
| CZ (1) | CZ2003482A3 (https=) |
| DE (1) | DE60128239T2 (https=) |
| DK (1) | DK1313716T3 (https=) |
| EA (1) | EA200300286A1 (https=) |
| EC (1) | ECSP034504A (https=) |
| ES (1) | ES2286137T3 (https=) |
| HU (1) | HUP0300857A3 (https=) |
| IL (1) | IL154110A0 (https=) |
| MX (1) | MXPA03001558A (https=) |
| NO (1) | NO20030729L (https=) |
| NZ (1) | NZ523804A (https=) |
| PL (1) | PL360744A1 (https=) |
| PT (1) | PT1313716E (https=) |
| SK (1) | SK1872003A3 (https=) |
| WO (1) | WO2002016331A1 (https=) |
| ZA (1) | ZA200300570B (https=) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE60129712T2 (de) * | 2000-08-23 | 2008-07-03 | Eli Lilly And Co., Indianapolis | Oxazolylaryloxyessigsäure derivate und ihre verwendung als ppar agonisten |
| EP1313717B1 (en) * | 2000-08-23 | 2007-10-17 | Eli Lilly And Company | Oxazolyl-arylpropionic acid derivatives and their use as ppar agonists |
| AU2002342244B2 (en) * | 2001-05-15 | 2005-06-16 | F. Hoffmann-La Roche Ag | Carboxylic acid substituted oxazole derivatives for use as PPAR-alpha and -gamma activators in the treatment of diabetes |
| KR100459917B1 (ko) * | 2001-12-14 | 2004-12-03 | (주)바이오뉴트리젠 | 페놀릭산 유도체 및 이를 포함하는 혈중 지질 농도 관련질환의 예방 및 치료용 조성물 |
| US6867224B2 (en) | 2002-03-07 | 2005-03-15 | Warner-Lambert Company | Compounds that modulate PPAR activity and methods of preparation |
| US6833380B2 (en) | 2002-03-07 | 2004-12-21 | Warner-Lambert Company, Llc | Compounds that modulate PPAR activity and methods of preparation |
| ES2291688T3 (es) | 2002-07-03 | 2008-03-01 | F. Hoffmann-La Roche Ag | Derivados de oxazol y su empleo como sensibilizadores a la insulina. |
| ES2350340T3 (es) * | 2002-08-30 | 2011-01-21 | F. Hoffmann-La Roche Ag | Nuevos compuestos de 2-aril-tiazol como agonistas de pparalfa y ppargamma. |
| NZ537979A (en) | 2002-09-12 | 2007-08-31 | Hoffmann La Roche | N-substituted-1H-indol-5-propionic acid compounds as PPAR agonists useful for the treatment of diabetes |
| AR041481A1 (es) * | 2002-10-07 | 2005-05-18 | Hoffmann La Roche | Derivados de acido arilpropionico-oxazol y su uso como agonistas de ppar |
| CN1711084B (zh) * | 2002-11-08 | 2010-04-28 | 霍夫曼-拉罗奇有限公司 | 作为ppar激动剂的取代4-烷氧基噁唑衍生物 |
| ATE405560T1 (de) | 2002-11-25 | 2008-09-15 | Hoffmann La Roche | Indolderivaten |
| DE10308355A1 (de) * | 2003-02-27 | 2004-12-23 | Aventis Pharma Deutschland Gmbh | Aryl-cycloalkyl substituierte Alkansäurederivate, Verfahren zu ihrer Herstellung und ihre Anwendung als Arzneimittel |
| US7244763B2 (en) | 2003-04-17 | 2007-07-17 | Warner Lambert Company Llc | Compounds that modulate PPAR activity and methods of preparation |
| ATE361294T1 (de) * | 2003-08-20 | 2007-05-15 | Lilly Co Eli | Verbindungen, verfahren und formulierungen zur oralen verabreichung einer glucagonartigen peptid (glp)-1-verbindung oder eines melanocortin-4- rezeptor-(mc4-)agonistschen peptids |
| CA2532026C (en) | 2003-08-20 | 2012-04-17 | Eli Lilly And Company | Compounds, methods and formulations for the oral delivery of a glucagon like peptide (glp)-1 compound or an melanocortin 4 receptor (mc4) agonist peptide |
| WO2005100318A1 (en) * | 2004-04-14 | 2005-10-27 | Ranbaxy Laboratories Limited | Alkanoic acids and their esters as antidiabetic agents |
| US20080051418A1 (en) * | 2004-11-26 | 2008-02-28 | Tsuyoshi Maekawa | Arylalkanoic Acid Derivative |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5089514A (en) * | 1990-06-14 | 1992-02-18 | Pfizer Inc. | 3-coxazolyl [phenyl, chromanyl or benzofuranyl]-2-hydroxypropionic acid derivatives and analogs as hypoglycemic agents |
| US5232945A (en) * | 1992-07-20 | 1993-08-03 | Pfizer Inc. | 3-aryl-2-hydroxypropionic acid derivatives and analogs as antihypertensives |
| US6062509A (en) | 1994-12-23 | 2000-05-16 | Hexcel Corporation | Retrofit centerline luggage bin assemblies compatible with existing aircraft bin supports |
| US5902726A (en) * | 1994-12-23 | 1999-05-11 | Glaxo Wellcome Inc. | Activators of the nuclear orphan receptor peroxisome proliferator-activated receptor gamma |
| EP0888278B1 (en) | 1996-02-02 | 2003-07-23 | Merck & Co., Inc. | Antidiabetic agents |
| GB9604242D0 (en) * | 1996-02-28 | 1996-05-01 | Glaxo Wellcome Inc | Chemical compounds |
| US6204277B1 (en) * | 1996-08-19 | 2001-03-20 | Japan Tobacco Inc. | Propionic acid derivatives and applications thereof |
| ATE451346T1 (de) | 1998-03-10 | 2009-12-15 | Ono Pharmaceutical Co | Carbonsäurederivate und medikamente die diese als aktiven wirkstoff enthalten |
| DE60005973T2 (de) | 1999-08-27 | 2004-05-13 | Eli Lilly And Co., Indianapolis | Biaryl-oxa(thia)zolderivate und ihre verwendung als ppars modulatoren |
| JP4316787B2 (ja) | 2000-01-11 | 2009-08-19 | 壽製薬株式会社 | エーテル又はアミド誘導体、その製法並びにそれを含有する糖尿病治療剤、 |
| DE60129712T2 (de) | 2000-08-23 | 2008-07-03 | Eli Lilly And Co., Indianapolis | Oxazolylaryloxyessigsäure derivate und ihre verwendung als ppar agonisten |
| EP1313717B1 (en) * | 2000-08-23 | 2007-10-17 | Eli Lilly And Company | Oxazolyl-arylpropionic acid derivatives and their use as ppar agonists |
-
2001
- 2001-08-23 HU HU0300857A patent/HUP0300857A3/hu unknown
- 2001-08-23 AU AU2001284659A patent/AU2001284659A1/en not_active Abandoned
- 2001-08-23 JP JP2002521432A patent/JP2004506721A/ja not_active Withdrawn
- 2001-08-23 EP EP01963733A patent/EP1313716B1/en not_active Expired - Lifetime
- 2001-08-23 KR KR10-2003-7002472A patent/KR20030027054A/ko not_active Withdrawn
- 2001-08-23 CA CA002418104A patent/CA2418104A1/en not_active Abandoned
- 2001-08-23 MX MXPA03001558A patent/MXPA03001558A/es unknown
- 2001-08-23 EA EA200300286A patent/EA200300286A1/ru unknown
- 2001-08-23 IL IL15411001A patent/IL154110A0/xx unknown
- 2001-08-23 PT PT01963733T patent/PT1313716E/pt unknown
- 2001-08-23 DE DE60128239T patent/DE60128239T2/de not_active Expired - Lifetime
- 2001-08-23 WO PCT/US2001/022616 patent/WO2002016331A1/en not_active Ceased
- 2001-08-23 NZ NZ523804A patent/NZ523804A/en unknown
- 2001-08-23 ES ES01963733T patent/ES2286137T3/es not_active Expired - Lifetime
- 2001-08-23 PL PL01360744A patent/PL360744A1/xx not_active Application Discontinuation
- 2001-08-23 DK DK01963733T patent/DK1313716T3/da active
- 2001-08-23 US US10/343,476 patent/US6930120B2/en not_active Expired - Fee Related
- 2001-08-23 SK SK187-2003A patent/SK1872003A3/sk not_active Application Discontinuation
- 2001-08-23 BR BR0113409-4A patent/BR0113409A/pt not_active IP Right Cessation
- 2001-08-23 AT AT01963733T patent/ATE361283T1/de not_active IP Right Cessation
- 2001-08-23 CZ CZ2003482A patent/CZ2003482A3/cs unknown
- 2001-08-23 CN CNA018177387A patent/CN1471517A/zh active Pending
-
2003
- 2003-01-21 ZA ZA200300570A patent/ZA200300570B/en unknown
- 2003-02-14 NO NO20030729A patent/NO20030729L/no not_active Application Discontinuation
- 2003-03-06 EC EC2003004504A patent/ECSP034504A/es unknown
-
2005
- 2005-02-09 US US11/054,226 patent/US7345070B2/en not_active Expired - Fee Related
-
2007
- 2007-06-19 CY CY20071100810T patent/CY1107679T1/el unknown
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