JP2005521741A5 - - Google Patents
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- Publication number
- JP2005521741A5 JP2005521741A5 JP2003582115A JP2003582115A JP2005521741A5 JP 2005521741 A5 JP2005521741 A5 JP 2005521741A5 JP 2003582115 A JP2003582115 A JP 2003582115A JP 2003582115 A JP2003582115 A JP 2003582115A JP 2005521741 A5 JP2005521741 A5 JP 2005521741A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- aryl
- hydrogen
- acetic acid
- methoxy
- 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.)
- Granted
Links
- 125000000217 alkyl group Chemical group 0.000 claims 41
- 125000003118 aryl group Chemical group 0.000 claims 24
- 229910052739 hydrogen Inorganic materials 0.000 claims 23
- 239000001257 hydrogen Substances 0.000 claims 23
- 150000002431 hydrogen Chemical class 0.000 claims 18
- 150000001875 compounds Chemical class 0.000 claims 15
- 125000003545 alkoxy group Chemical group 0.000 claims 12
- 229910052736 halogen Inorganic materials 0.000 claims 10
- 150000002367 halogens Chemical class 0.000 claims 10
- 125000003342 alkenyl group Chemical group 0.000 claims 9
- 125000000304 alkynyl group Chemical group 0.000 claims 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims 9
- 125000001188 haloalkyl group Chemical group 0.000 claims 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 9
- 125000004429 atom Chemical group 0.000 claims 6
- 125000005842 heteroatom Chemical group 0.000 claims 6
- 239000008194 pharmaceutical composition Substances 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- 241000124008 Mammalia Species 0.000 claims 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims 5
- 239000000203 mixture Substances 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 229920006395 saturated elastomer Polymers 0.000 claims 3
- 125000003107 substituted aryl group Chemical group 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- 125000001054 5 membered carbocyclic group Chemical group 0.000 claims 2
- -1 5-trifluoromethyl - pyridin-2-yl Chemical group 0.000 claims 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 2
- 230000002152 alkylating effect Effects 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 229930195733 hydrocarbon Natural products 0.000 claims 2
- 150000002430 hydrocarbons Chemical class 0.000 claims 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims 2
- 150000003573 thiols Chemical class 0.000 claims 2
- VFQRJNOXLNYYTE-UHFFFAOYSA-N 2-[3-methoxy-4-[[4-[4-(trifluoromethyl)phenyl]phenyl]methylsulfanyl]phenoxy]acetic acid Chemical compound COC1=CC(OCC(O)=O)=CC=C1SCC1=CC=C(C=2C=CC(=CC=2)C(F)(F)F)C=C1 VFQRJNOXLNYYTE-UHFFFAOYSA-N 0.000 claims 1
- QZCOZWYSOAUBJR-UHFFFAOYSA-N 2-[4-[[4-(2,4-dichlorophenyl)phenyl]methylsulfanyl]-5-methoxy-2-methylphenoxy]acetic acid Chemical compound COC1=CC(OCC(O)=O)=C(C)C=C1SCC1=CC=C(C=2C(=CC(Cl)=CC=2)Cl)C=C1 QZCOZWYSOAUBJR-UHFFFAOYSA-N 0.000 claims 1
- UXBLXTMVLIEOGI-UHFFFAOYSA-N 2-[4-[[4-(4-fluorophenyl)phenyl]methylsulfanyl]-5-methoxy-2-methylphenoxy]acetic acid Chemical compound COC1=CC(OCC(O)=O)=C(C)C=C1SCC1=CC=C(C=2C=CC(F)=CC=2)C=C1 UXBLXTMVLIEOGI-UHFFFAOYSA-N 0.000 claims 1
- QPQVDUHBPMLTTD-UHFFFAOYSA-N 2-[4-[[4-[2-(3-fluorophenyl)ethenyl]phenyl]methylsulfanyl]-5-methoxy-2-methylphenoxy]acetic acid Chemical compound COC1=CC(OCC(O)=O)=C(C)C=C1SCC(C=C1)=CC=C1C=CC1=CC=CC(F)=C1 QPQVDUHBPMLTTD-UHFFFAOYSA-N 0.000 claims 1
- JLQGDIDQGNXZJJ-UHFFFAOYSA-N 2-[4-[[5-(4-chlorophenyl)-1,2-oxazol-3-yl]methylsulfanyl]-5-methoxy-2-methylphenoxy]acetic acid Chemical compound COC1=CC(OCC(O)=O)=C(C)C=C1SCC1=NOC(C=2C=CC(Cl)=CC=2)=C1 JLQGDIDQGNXZJJ-UHFFFAOYSA-N 0.000 claims 1
- COOMMSHFMOKEKM-UHFFFAOYSA-N 2-[5-methoxy-2-methyl-4-[(4-phenylphenyl)methylsulfanyl]phenoxy]acetic acid Chemical compound COC1=CC(OCC(O)=O)=C(C)C=C1SCC1=CC=C(C=2C=CC=CC=2)C=C1 COOMMSHFMOKEKM-UHFFFAOYSA-N 0.000 claims 1
- AJQNSRYZFLLBOI-UHFFFAOYSA-N 2-[5-methoxy-2-methyl-4-[2-[4-[4-(trifluoromethyl)phenyl]phenyl]ethylsulfanyl]phenoxy]acetic acid Chemical compound COC1=CC(OCC(O)=O)=C(C)C=C1SCCC1=CC=C(C=2C=CC(=CC=2)C(F)(F)F)C=C1 AJQNSRYZFLLBOI-UHFFFAOYSA-N 0.000 claims 1
- HXCKESKWJSVFAR-UHFFFAOYSA-N 2-[5-methoxy-2-methyl-4-[[2-methyl-4-[4-(trifluoromethyl)phenyl]phenyl]methylsulfanyl]phenoxy]acetic acid Chemical compound COC1=CC(OCC(O)=O)=C(C)C=C1SCC1=CC=C(C=2C=CC(=CC=2)C(F)(F)F)C=C1C HXCKESKWJSVFAR-UHFFFAOYSA-N 0.000 claims 1
- VVUWGDAIOYKXPE-UHFFFAOYSA-N 2-[5-methoxy-2-methyl-4-[[3-[3-(trifluoromethoxy)phenyl]phenyl]methylsulfanyl]phenoxy]acetic acid Chemical compound COC1=CC(OCC(O)=O)=C(C)C=C1SCC1=CC=CC(C=2C=C(OC(F)(F)F)C=CC=2)=C1 VVUWGDAIOYKXPE-UHFFFAOYSA-N 0.000 claims 1
- GSPKTIOMMLSIHT-UHFFFAOYSA-N 2-[5-methoxy-2-methyl-4-[[3-[4-(trifluoromethyl)phenyl]-1,2-oxazol-5-yl]methylsulfanyl]phenoxy]acetic acid Chemical compound COC1=CC(OCC(O)=O)=C(C)C=C1SCC1=CC(C=2C=CC(=CC=2)C(F)(F)F)=NO1 GSPKTIOMMLSIHT-UHFFFAOYSA-N 0.000 claims 1
- MANTXHYUNLPBHE-UHFFFAOYSA-N 2-[5-methoxy-2-methyl-4-[[3-[4-(trifluoromethyl)phenyl]phenyl]methylsulfanyl]phenoxy]acetic acid Chemical compound COC1=CC(OCC(O)=O)=C(C)C=C1SCC1=CC=CC(C=2C=CC(=CC=2)C(F)(F)F)=C1 MANTXHYUNLPBHE-UHFFFAOYSA-N 0.000 claims 1
- WPLMYOVJSNXPMK-UHFFFAOYSA-N 2-[5-methoxy-2-methyl-4-[[4-[3-(trifluoromethyl)phenyl]phenyl]methylsulfanyl]phenoxy]acetic acid Chemical compound COC1=CC(OCC(O)=O)=C(C)C=C1SCC1=CC=C(C=2C=C(C=CC=2)C(F)(F)F)C=C1 WPLMYOVJSNXPMK-UHFFFAOYSA-N 0.000 claims 1
- YBYRUZQLTYRCRF-UHFFFAOYSA-N 2-[5-methoxy-2-methyl-4-[[4-[4-(trifluoromethyl)phenyl]phenyl]methylsulfanyl]phenoxy]acetic acid Chemical compound COC1=CC(OCC(O)=O)=C(C)C=C1SCC1=CC=C(C=2C=CC(=CC=2)C(F)(F)F)C=C1 YBYRUZQLTYRCRF-UHFFFAOYSA-N 0.000 claims 1
- NWEHHVVXCHVPFQ-UHFFFAOYSA-N 2-[5-methoxy-2-methyl-4-[[4-[5-(trifluoromethyl)pyridin-2-yl]phenyl]methylsulfanyl]phenoxy]acetic acid Chemical compound COC1=CC(OCC(O)=O)=C(C)C=C1SCC1=CC=C(C=2N=CC(=CC=2)C(F)(F)F)C=C1 NWEHHVVXCHVPFQ-UHFFFAOYSA-N 0.000 claims 1
- ONKOHQZZVMTPOM-UHFFFAOYSA-N 2-[5-methoxy-2-methyl-4-[[4-[[4-(trifluoromethyl)phenyl]methoxy]phenyl]methylsulfanyl]phenoxy]acetic acid Chemical compound COC1=CC(OCC(O)=O)=C(C)C=C1SCC(C=C1)=CC=C1OCC1=CC=C(C(F)(F)F)C=C1 ONKOHQZZVMTPOM-UHFFFAOYSA-N 0.000 claims 1
- WIOTZGHDAYUCBC-UHFFFAOYSA-N 2-[5-methoxy-2-methyl-4-[[5-[4-(trifluoromethyl)phenyl]-1,2-oxazol-3-yl]methylsulfanyl]phenoxy]acetic acid Chemical compound COC1=CC(OCC(O)=O)=C(C)C=C1SCC1=NOC(C=2C=CC(=CC=2)C(F)(F)F)=C1 WIOTZGHDAYUCBC-UHFFFAOYSA-N 0.000 claims 1
- HEMOEZGWSUFMTR-UHFFFAOYSA-N 2-[5-methoxy-2-methyl-4-[[6-[4-(trifluoromethyl)phenyl]pyridin-3-yl]methylsulfanyl]phenoxy]acetic acid Chemical compound COC1=CC(OCC(O)=O)=C(C)C=C1SCC1=CC=C(C=2C=CC(=CC=2)C(F)(F)F)N=C1 HEMOEZGWSUFMTR-UHFFFAOYSA-N 0.000 claims 1
- UUBMLUGVHDOXPD-UHFFFAOYSA-N 2-[[7-[[4-[4-(trifluoromethyl)phenyl]phenyl]methylsulfanyl]-2,3-dihydro-1h-inden-4-yl]oxy]acetic acid Chemical compound C1=2CCCC=2C(OCC(=O)O)=CC=C1SCC(C=C1)=CC=C1C1=CC=C(C(F)(F)F)C=C1 UUBMLUGVHDOXPD-UHFFFAOYSA-N 0.000 claims 1
- IVINVXPMKZERSK-UHFFFAOYSA-N 2-[[7-[[4-[[4-(trifluoromethyl)phenyl]methoxy]phenyl]methylsulfanyl]-2,3-dihydro-1h-inden-4-yl]oxy]acetic acid Chemical compound C1=2CCCC=2C(OCC(=O)O)=CC=C1SCC(C=C1)=CC=C1OCC1=CC=C(C(F)(F)F)C=C1 IVINVXPMKZERSK-UHFFFAOYSA-N 0.000 claims 1
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- 208000032928 Dyslipidaemia Diseases 0.000 claims 1
- 208000035150 Hypercholesterolemia Diseases 0.000 claims 1
- 102000016267 Leptin Human genes 0.000 claims 1
- 108010092277 Leptin Proteins 0.000 claims 1
- 208000017170 Lipid metabolism disease Diseases 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 150000002148 esters Chemical group 0.000 claims 1
- NRYBAZVQPHGZNS-ZSOCWYAHSA-N leptin Chemical compound O=C([C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)CNC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](N)CC(C)C)CCSC)N1CCC[C@H]1C(=O)NCC(=O)N[C@@H](CS)C(O)=O NRYBAZVQPHGZNS-ZSOCWYAHSA-N 0.000 claims 1
- 229940039781 leptin Drugs 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 229930195734 saturated hydrocarbon Natural products 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US37050802P | 2002-04-05 | 2002-04-05 | |
| US38602602P | 2002-06-05 | 2002-06-05 | |
| PCT/IB2003/001121 WO2003084916A2 (en) | 2002-04-05 | 2003-03-24 | Compounds that modulate ppar activity and methods for their preparation |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2005360431A Division JP2006151985A (ja) | 2002-04-05 | 2005-12-14 | Ｐｐａｒ活性を調節する化合物、及び該化合物の製造方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2005521741A JP2005521741A (ja) | 2005-07-21 |
| JP2005521741A5 true JP2005521741A5 (enExample) | 2005-12-22 |
| JP3816922B2 JP3816922B2 (ja) | 2006-08-30 |
Family
ID=28794388
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003582115A Expired - Fee Related JP3816922B2 (ja) | 2002-04-05 | 2003-03-24 | Ｐｐａｒ活性を調節する化合物、及び該化合物の製造方法 |
| JP2005360431A Withdrawn JP2006151985A (ja) | 2002-04-05 | 2005-12-14 | Ｐｐａｒ活性を調節する化合物、及び該化合物の製造方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2005360431A Withdrawn JP2006151985A (ja) | 2002-04-05 | 2005-12-14 | Ｐｐａｒ活性を調節する化合物、及び該化合物の製造方法 |
Country Status (35)
Families Citing this family (86)
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| AU2003296404A1 (en) * | 2003-01-06 | 2004-08-10 | Eli Lilly And Company | Heterocyclic ppar modulators |
| US7244763B2 (en) * | 2003-04-17 | 2007-07-17 | Warner Lambert Company Llc | Compounds that modulate PPAR activity and methods of preparation |
| EP1630152A4 (en) * | 2003-05-30 | 2009-09-23 | Takeda Pharmaceutical | CONDENSED CYCLIC COMPOUND |
| PL1667964T3 (pl) | 2003-09-19 | 2010-01-29 | Janssen Pharmaceutica Nv | Kwasy 4-((fenoksyalkilo)tio)-fenoksyoctowe i analogi |
| BRPI0414554A (pt) * | 2003-10-28 | 2006-11-07 | Reddys Lab Ltd Dr | compostos e seus usos em medicina: processo para preparação destes e composições farmacêuticas que os contenham |
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| JP2007509998A (ja) | 2003-11-05 | 2007-04-19 | エフ．ホフマン−ラ ロシュ アーゲー | Ｐｐａｒ活性化剤としてのベンズ環付加された化合物 |
| CN100509802C (zh) | 2003-11-05 | 2009-07-08 | 霍夫曼-拉罗奇有限公司 | 作为ppar激活剂的杂芳基衍生物 |
| KR20080042188A (ko) * | 2003-11-05 | 2008-05-14 | 에프. 호프만-라 로슈 아게 | Ｐｐａｒ 작용제로서 페닐 유도체 |
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| ATE486055T1 (de) * | 2004-05-05 | 2010-11-15 | High Point Pharmaceuticals Llc | Neue verbindungen, ihre herstellung und verwendung |
| DE602005022585D1 (de) * | 2004-05-05 | 2010-09-09 | High Point Pharmaceuticals Llc | Phenoxyessigsäurederivate als ppar-agonisten |
| BRPI0510024A (pt) * | 2004-05-14 | 2007-09-25 | Irm Llc | compostos e composições como modulares de ppar |
| US7820705B2 (en) * | 2004-05-14 | 2010-10-26 | Irm Llc | Compounds and compositions as PPAR modulators |
| US20070232647A1 (en) * | 2004-05-25 | 2007-10-04 | Goetze Leopold F | Use of Ppar Agonists to Treat Ruminants |
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| CN101007798B (zh) * | 2006-01-24 | 2011-01-26 | 中国人民解放军军事医学科学院毒物药物研究所 | 苯并间二氧杂环戊烯衍生物及其制备方法和医药用途 |
| JP2009529512A (ja) * | 2006-03-09 | 2009-08-20 | ハイ ポイント ファーマシューティカルズ，リミティド ライアビリティ カンパニー | 新規な化合物、それらの製造法、及び使用法 |
| US8383660B2 (en) | 2006-03-10 | 2013-02-26 | Pfizer Inc. | Dibenzyl amine compounds and derivatives |
| JP2009530281A (ja) * | 2006-03-14 | 2009-08-27 | アムジエン・インコーポレーテツド | 代謝障害の治療に有用である二環式カルボン酸誘導体 |
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- 2003-03-24 CN CNA038097915A patent/CN1649820A/zh active Pending
- 2003-03-24 HR HRP20040916 patent/HRP20040916A2/hr not_active Application Discontinuation
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