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- Withdrawn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 (enExample) | 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 (enExample) |
| EP (1) | EP1313716B1 (enExample) |
| JP (1) | JP2004506721A (enExample) |
| KR (1) | KR20030027054A (enExample) |
| CN (1) | CN1471517A (enExample) |
| AT (1) | ATE361283T1 (enExample) |
| AU (1) | AU2001284659A1 (enExample) |
| BR (1) | BR0113409A (enExample) |
| CA (1) | CA2418104A1 (enExample) |
| CY (1) | CY1107679T1 (enExample) |
| CZ (1) | CZ2003482A3 (enExample) |
| DE (1) | DE60128239T2 (enExample) |
| DK (1) | DK1313716T3 (enExample) |
| EA (1) | EA200300286A1 (enExample) |
| EC (1) | ECSP034504A (enExample) |
| ES (1) | ES2286137T3 (enExample) |
| HU (1) | HUP0300857A3 (enExample) |
| IL (1) | IL154110A0 (enExample) |
| MX (1) | MXPA03001558A (enExample) |
| NO (1) | NO20030729L (enExample) |
| NZ (1) | NZ523804A (enExample) |
| PL (1) | PL360744A1 (enExample) |
| PT (1) | PT1313716E (enExample) |
| SK (1) | SK1872003A3 (enExample) |
| WO (1) | WO2002016331A1 (enExample) |
| ZA (1) | ZA200300570B (enExample) |
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 |
| ES2295200T3 (es) | 2000-08-23 | 2008-04-16 | Eli Lilly And Company | Derivados de acido oxazolil-arilpropionico y su uso como agonistas de ppar. |
| ME01310B (me) * | 2001-05-15 | 2011-10-10 | Hoffmann La Roche | Derivati oksazola koji su supstituisani karboksilnom kiselinom za primenu kao ppar-alfa-1-gama aktivatori u lečenju dijabetesa |
| KR100459917B1 (ko) * | 2001-12-14 | 2004-12-03 | (주)바이오뉴트리젠 | 페놀릭산 유도체 및 이를 포함하는 혈중 지질 농도 관련질환의 예방 및 치료용 조성물 |
| US6833380B2 (en) | 2002-03-07 | 2004-12-21 | Warner-Lambert Company, Llc | Compounds that modulate PPAR activity and methods of preparation |
| US6867224B2 (en) | 2002-03-07 | 2005-03-15 | Warner-Lambert Company | Compounds that modulate PPAR activity and methods of preparation |
| ATE372990T1 (de) | 2002-07-03 | 2007-09-15 | Hoffmann La Roche | Oxazolderivat und deren verwendung als insulinsensibilisatoren |
| CN100475810C (zh) * | 2002-08-30 | 2009-04-08 | 霍夫曼-拉罗奇有限公司 | 作为PPARα和PPARγ激动剂的新型2-芳基噻唑化合物 |
| 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 |
| TWI343915B (en) * | 2002-10-07 | 2011-06-21 | Hoffmann La Roche | Chirale ppar agonists |
| ES2295692T3 (es) * | 2002-11-08 | 2008-04-16 | F. Hoffmann-La Roche Ag | Nuevos derivados de 4-alcoxioxazol sustituido como agonistas de ppar. |
| MXPA05005445A (es) | 2002-11-25 | 2005-08-26 | Hoffmann La Roche | Derivados de indolilo. |
| 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 |
| JP4767850B2 (ja) | 2003-08-20 | 2011-09-07 | エミスフィアー テクノロジーズ インコーポレイテッド | グルカゴン様ペプチド（ｇｌｐ）−１化合物またはメラノコルチン４受容体（ｍｃ４）アゴニストペプチドの経口デリバリーのための化合物、方法および製剤 |
| CN100398536C (zh) * | 2003-08-20 | 2008-07-02 | 爱密斯菲尔科技公司 | 用于口服传递glp-1化合物或mc4激动剂肽的化合物、方法和制剂 |
| 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 |
| US5902726A (en) | 1994-12-23 | 1999-05-11 | Glaxo Wellcome Inc. | Activators of the nuclear orphan receptor peroxisome proliferator-activated receptor gamma |
| US6062509A (en) | 1994-12-23 | 2000-05-16 | Hexcel Corporation | Retrofit centerline luggage bin assemblies compatible with existing aircraft bin supports |
| DE69723680T9 (de) | 1996-02-02 | 2004-11-04 | Merck & Co., Inc. | Antidiabetische mittel |
| GB9604242D0 (en) | 1996-02-28 | 1996-05-01 | Glaxo Wellcome Inc | Chemical compounds |
| IL128600A0 (en) * | 1996-08-19 | 2000-01-31 | Japan Tobacco Inc | Propionic acid derivatives and pharmaceutical compositions containing them |
| JP4345230B2 (ja) | 1998-03-10 | 2009-10-14 | 小野薬品工業株式会社 | カルボン酸誘導体およびその誘導体を有効成分として含有する薬剤 |
| DK1206457T3 (da) | 1999-08-27 | 2004-02-16 | Lilly Co Eli | Biaryl-oxa(thia)zolderivater og deres anvendelse som modulatorer PPAP'ER |
| 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 |
| ES2295200T3 (es) | 2000-08-23 | 2008-04-16 | Eli Lilly And Company | Derivados de acido oxazolil-arilpropionico y su uso como agonistas de ppar. |
-
2001
- 2001-08-23 CA CA002418104A patent/CA2418104A1/en not_active Abandoned
- 2001-08-23 CN CNA018177387A patent/CN1471517A/zh active Pending
- 2001-08-23 DE DE60128239T patent/DE60128239T2/de not_active Expired - Lifetime
- 2001-08-23 MX MXPA03001558A patent/MXPA03001558A/es unknown
- 2001-08-23 DK DK01963733T patent/DK1313716T3/da active
- 2001-08-23 WO PCT/US2001/022616 patent/WO2002016331A1/en not_active Ceased
- 2001-08-23 IL IL15411001A patent/IL154110A0/xx unknown
- 2001-08-23 EA EA200300286A patent/EA200300286A1/ru unknown
- 2001-08-23 AT AT01963733T patent/ATE361283T1/de not_active IP Right Cessation
- 2001-08-23 EP EP01963733A patent/EP1313716B1/en not_active Expired - Lifetime
- 2001-08-23 HU HU0300857A patent/HUP0300857A3/hu unknown
- 2001-08-23 PT PT01963733T patent/PT1313716E/pt unknown
- 2001-08-23 AU AU2001284659A patent/AU2001284659A1/en not_active Abandoned
- 2001-08-23 NZ NZ523804A patent/NZ523804A/en unknown
- 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 JP JP2002521432A patent/JP2004506721A/ja not_active Withdrawn
- 2001-08-23 BR BR0113409-4A patent/BR0113409A/pt not_active IP Right Cessation
- 2001-08-23 PL PL01360744A patent/PL360744A1/xx not_active Application Discontinuation
- 2001-08-23 CZ CZ2003482A patent/CZ2003482A3/cs unknown
- 2001-08-23 KR KR10-2003-7002472A patent/KR20030027054A/ko not_active Withdrawn
- 2001-08-23 ES ES01963733T patent/ES2286137T3/es not_active Expired - Lifetime
-
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