SK1872003A3 - Oxazolyl-arylpropionic acid derivatives and their use as PPAR agonists - Google Patents

Oxazolyl-arylpropionic acid derivatives and their use as PPAR agonists Download PDF

Info

Publication number: SK1872003A3
Authority: SK; Slovakia
Prior art keywords: methyl; phenyl; compound; oxazol; ethoxy
Prior art date: 2000-08-23

Application number

SK187-2003A

Other languages

English (en)

Slovak (sk)

Inventor

Dawn Alisa Brooks

Alexander Glenn Godfrey

Sarah Beth Jones

James Ray Mccarthy

Christopher John Rito

Leonard Larry Winneroski Jr

Yanping Xu

Original Assignee

Lilly Co Eli

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.)

2000-08-23

Filing date

2001-08-23

Publication date

2003-07-01

2001-08-23 Application filed by Lilly Co Eli filed Critical Lilly Co Eli

2003-07-01 Publication of SK1872003A3 publication Critical patent/SK1872003A3/sk

Links

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239000000556 agonist Substances 0.000 title description 6
150000001875 compounds Chemical class 0.000 claims abstract description 307
-1 thiophen-2,5-diyl Chemical group 0.000 claims abstract description 152
150000003839 salts Chemical class 0.000 claims abstract description 59
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 40
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238000011282 treatment Methods 0.000 claims abstract description 24
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125000005493 quinolyl group Chemical group 0.000 claims abstract description 9
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125000001072 heteroaryl group Chemical group 0.000 claims abstract description 8
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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 claims 1
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URMFZWYYVWAECJ-PMERELPUSA-N ethyl (2s)-2-[[4-[2-[5-methyl-2-(5-methylthiophen-2-yl)-1,3-oxazol-4-yl]ethoxy]phenyl]methyl]-2-phenoxybutanoate Chemical compound C([C@@](CC)(C(=O)OCC)OC=1C=CC=CC=1)C(C=C1)=CC=C1OCCC(=C(O1)C)N=C1C1=CC=C(C)S1 URMFZWYYVWAECJ-PMERELPUSA-N 0.000 description 2
LWKFJXIQVCIRRT-SFHVURJKSA-N ethyl (2s)-3-(4-hydroxyphenyl)-2-methyl-2-[4-(trifluoromethyl)phenoxy]propanoate Chemical compound C([C@@](C)(C(=O)OCC)OC=1C=CC(=CC=1)C(F)(F)F)C1=CC=C(O)C=C1 LWKFJXIQVCIRRT-SFHVURJKSA-N 0.000 description 2
KBQOZXKDJFZITE-UHFFFAOYSA-N ethyl 2-(2-fluorophenoxy)-3-(4-hydroxyphenyl)-2-methylpropanoate Chemical compound C=1C=CC=C(F)C=1OC(C)(C(=O)OCC)CC1=CC=C(O)C=C1 KBQOZXKDJFZITE-UHFFFAOYSA-N 0.000 description 2
LPQPDBRKMMUTOB-UHFFFAOYSA-N ethyl 2-(3-bromophenoxy)-2-methyl-3-(4-phenylmethoxyphenyl)propanoate Chemical compound C=1C=CC(Br)=CC=1OC(C)(C(=O)OCC)CC(C=C1)=CC=C1OCC1=CC=CC=C1 LPQPDBRKMMUTOB-UHFFFAOYSA-N 0.000 description 2
QIHURAKGRREUED-UHFFFAOYSA-N ethyl 2-(3-bromophenoxy)-3-(4-hydroxyphenyl)-2-methylpropanoate Chemical compound C=1C=CC(Br)=CC=1OC(C)(C(=O)OCC)CC1=CC=C(O)C=C1 QIHURAKGRREUED-UHFFFAOYSA-N 0.000 description 2
RESIMVHPPWLYKG-UHFFFAOYSA-N ethyl 2-(3-fluorophenoxy)-3-(4-hydroxyphenyl)-2-methylpropanoate Chemical compound C=1C=CC(F)=CC=1OC(C)(C(=O)OCC)CC1=CC=C(O)C=C1 RESIMVHPPWLYKG-UHFFFAOYSA-N 0.000 description 2
LOKCSHZKKBANHP-UHFFFAOYSA-N ethyl 2-(4-chlorophenoxy)-3-(4-hydroxyphenyl)-2-methylpropanoate Chemical compound C=1C=C(Cl)C=CC=1OC(C)(C(=O)OCC)CC1=CC=C(O)C=C1 LOKCSHZKKBANHP-UHFFFAOYSA-N 0.000 description 2
OWQRUGUGNVFZQQ-UHFFFAOYSA-N ethyl 2-(4-cyclohexylphenoxy)-3-(4-hydroxyphenyl)-2-methylpropanoate Chemical compound C=1C=C(C2CCCCC2)C=CC=1OC(C)(C(=O)OCC)CC1=CC=C(O)C=C1 OWQRUGUGNVFZQQ-UHFFFAOYSA-N 0.000 description 2
ZGFMBUHREWMBOI-UHFFFAOYSA-N ethyl 2-(4-methoxyphenoxy)propanoate Chemical compound CCOC(=O)C(C)OC1=CC=C(OC)C=C1 ZGFMBUHREWMBOI-UHFFFAOYSA-N 0.000 description 2
FPNJNATVJJNSIL-UHFFFAOYSA-N ethyl 2-[(4-hydroxyphenyl)methyl]-2-phenoxybutanoate Chemical compound C=1C=CC=CC=1OC(CC)(C(=O)OCC)CC1=CC=C(O)C=C1 FPNJNATVJJNSIL-UHFFFAOYSA-N 0.000 description 2
XMZODYMJRDGESZ-UHFFFAOYSA-N ethyl 2-methyl-2-phenoxy-3-(4-prop-2-enoxyphenyl)propanoate Chemical compound C=1C=CC=CC=1OC(C)(C(=O)OCC)CC1=CC=C(OCC=C)C=C1 XMZODYMJRDGESZ-UHFFFAOYSA-N 0.000 description 2
XHVWILOVPDMSQT-UHFFFAOYSA-N ethyl 2-methyl-3-(4-phenylmethoxyphenyl)-2-quinolin-6-yloxypropanoate Chemical compound C=1C=C2N=CC=CC2=CC=1OC(C)(C(=O)OCC)CC(C=C1)=CC=C1OCC1=CC=CC=C1 XHVWILOVPDMSQT-UHFFFAOYSA-N 0.000 description 2
HHVSGFGIRONLDV-UHFFFAOYSA-N ethyl 2-methyl-3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]-2-phenoxypropanoate Chemical compound C=1C=CC=CC=1OC(C)(C(=O)OCC)CC(C=C1)=CC=C1OCCC(=C(O1)C)N=C1C1=CC=CC=C1 HHVSGFGIRONLDV-UHFFFAOYSA-N 0.000 description 2
HHGQIGYKEKXZCA-UHFFFAOYSA-N ethyl 2-quinolin-6-yloxypropanoate Chemical compound N1=CC=CC2=CC(OC(C)C(=O)OCC)=CC=C21 HHGQIGYKEKXZCA-UHFFFAOYSA-N 0.000 description 2
CFKWPYWULHFOBA-UHFFFAOYSA-N ethyl 3-(4-hydroxy-3-methoxyphenyl)-2-methyl-2-phenoxypropanoate Chemical compound C=1C=CC=CC=1OC(C)(C(=O)OCC)CC1=CC=C(O)C(OC)=C1 CFKWPYWULHFOBA-UHFFFAOYSA-N 0.000 description 2
QKEXRNJCFDGBNV-UHFFFAOYSA-N ethyl 3-(4-hydroxy-3-prop-2-enylphenyl)-2-methyl-2-phenoxypropanoate Chemical compound C=1C=CC=CC=1OC(C)(C(=O)OCC)CC1=CC=C(O)C(CC=C)=C1 QKEXRNJCFDGBNV-UHFFFAOYSA-N 0.000 description 2
NQICOBWWSNOFTC-UHFFFAOYSA-N ethyl 3-(4-hydroxy-3-propylphenyl)-2-methyl-2-phenoxypropanoate Chemical compound C1=C(O)C(CCC)=CC(CC(C)(OC=2C=CC=CC=2)C(=O)OCC)=C1 NQICOBWWSNOFTC-UHFFFAOYSA-N 0.000 description 2
ZVDYEIHGOSPQET-UHFFFAOYSA-N ethyl 3-(4-hydroxyphenyl)-2-methyl-2-(2-methylphenoxy)propanoate Chemical compound C=1C=CC=C(C)C=1OC(C)(C(=O)OCC)CC1=CC=C(O)C=C1 ZVDYEIHGOSPQET-UHFFFAOYSA-N 0.000 description 2
JLYDSUBJJPCLKN-UHFFFAOYSA-N ethyl 3-(4-hydroxyphenyl)-2-methyl-2-[4-(trifluoromethoxy)phenoxy]propanoate Chemical compound C=1C=C(OC(F)(F)F)C=CC=1OC(C)(C(=O)OCC)CC1=CC=C(O)C=C1 JLYDSUBJJPCLKN-UHFFFAOYSA-N 0.000 description 2
LWKFJXIQVCIRRT-UHFFFAOYSA-N ethyl 3-(4-hydroxyphenyl)-2-methyl-2-[4-(trifluoromethyl)phenoxy]propanoate Chemical compound C=1C=C(C(F)(F)F)C=CC=1OC(C)(C(=O)OCC)CC1=CC=C(O)C=C1 LWKFJXIQVCIRRT-UHFFFAOYSA-N 0.000 description 2
GOPUYMQNOOZOET-UHFFFAOYSA-N ethyl 3-[4-[2-(2-cyclohexyl-5-methyl-1,3-oxazol-4-yl)ethoxy]phenyl]-2-methyl-2-(3-phenylphenoxy)propanoate Chemical compound C=1C=CC(C=2C=CC=CC=2)=CC=1OC(C)(C(=O)OCC)CC(C=C1)=CC=C1OCCC(=C(O1)C)N=C1C1CCCCC1 GOPUYMQNOOZOET-UHFFFAOYSA-N 0.000 description 2
FTJYNBFGEHBRKX-UHFFFAOYSA-N ethyl 3-hydroxy-2-methyl-2-phenoxy-3-(4-phenylmethoxyphenyl)propanoate Chemical compound C=1C=C(OCC=2C=CC=CC=2)C=CC=1C(O)C(C)(C(=O)OCC)OC1=CC=CC=C1 FTJYNBFGEHBRKX-UHFFFAOYSA-N 0.000 description 2
GFTYVNARAIUWID-UHFFFAOYSA-N ethyl 3-hydroxy-2-methyl-3-(4-phenylmethoxyphenyl)-2-quinolin-6-yloxypropanoate Chemical compound C=1C=C2N=CC=CC2=CC=1OC(C)(C(=O)OCC)C(O)C(C=C1)=CC=C1OCC1=CC=CC=C1 GFTYVNARAIUWID-UHFFFAOYSA-N 0.000 description 2
FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 2
239000010685 fatty oil Substances 0.000 description 2
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125000005843 halogen group Chemical group 0.000 description 2
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238000000338 in vitro Methods 0.000 description 2
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238000007918 intramuscular administration Methods 0.000 description 2
238000001990 intravenous administration Methods 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
229960002725 isoflurane Drugs 0.000 description 2
229910052744 lithium Inorganic materials 0.000 description 2
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229910052751 metal Inorganic materials 0.000 description 2
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IDVDTNDUXYNAMS-UHFFFAOYSA-N methyl 2-[5-methyl-2-(2-phenylethyl)-1,3-oxazol-4-yl]acetate Chemical compound O1C(C)=C(CC(=O)OC)N=C1CCC1=CC=CC=C1 IDVDTNDUXYNAMS-UHFFFAOYSA-N 0.000 description 2
PFFHWUQMSVPUIP-UHFFFAOYSA-N methyl 2-[5-methyl-2-(5-methylthiophen-2-yl)-1,3-oxazol-4-yl]acetate Chemical compound O1C(C)=C(CC(=O)OC)N=C1C1=CC=C(C)S1 PFFHWUQMSVPUIP-UHFFFAOYSA-N 0.000 description 2
RDQOZYXDCSNDQD-UHFFFAOYSA-N methyl 2-methyl-2-phenoxy-3-thiophen-2-ylpropanoate Chemical compound C=1C=CC=CC=1OC(C)(C(=O)OC)CC1=CC=CS1 RDQOZYXDCSNDQD-UHFFFAOYSA-N 0.000 description 2
WZRXAFCAACJXGY-UHFFFAOYSA-N methyl 2-methyl-3-[5-[3-(5-methyl-2-phenyl-1,3-oxazol-4-yl)propanoyl]thiophen-2-yl]-2-phenoxypropanoate Chemical compound C=1C=CC=CC=1OC(C)(C(=O)OC)CC(S1)=CC=C1C(=O)CCC(=C(O1)C)N=C1C1=CC=CC=C1 WZRXAFCAACJXGY-UHFFFAOYSA-N 0.000 description 2
LTCILDSAFPQUBF-UHFFFAOYSA-N methyl 2-methyl-3-[5-[3-(5-methyl-2-phenyl-1,3-oxazol-4-yl)propyl]thiophen-2-yl]-2-phenoxypropanoate Chemical compound C=1C=CC=CC=1OC(C)(C(=O)OC)CC(S1)=CC=C1CCCC(=C(O1)C)N=C1C1=CC=CC=C1 LTCILDSAFPQUBF-UHFFFAOYSA-N 0.000 description 2
ZBYKBOXEALNKCQ-UHFFFAOYSA-N methyl 3-[(5-methylthiophene-2-carbonyl)amino]-4-oxopentanoate Chemical compound COC(=O)CC(C(C)=O)NC(=O)C1=CC=C(C)S1 ZBYKBOXEALNKCQ-UHFFFAOYSA-N 0.000 description 2
UNIBYUONEMQGSR-UHFFFAOYSA-N methyl 3-[5-[1-hydroxy-3-(5-methyl-2-phenyl-1,3-oxazol-4-yl)propyl]thiophen-2-yl]-2-methyl-2-phenoxypropanoate Chemical compound C=1C=CC=CC=1OC(C)(C(=O)OC)CC(S1)=CC=C1C(O)CCC(=C(O1)C)N=C1C1=CC=CC=C1 UNIBYUONEMQGSR-UHFFFAOYSA-N 0.000 description 2
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NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 2
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UXCDUFKZSUBXGM-UHFFFAOYSA-N phosphoric tribromide Chemical compound BrP(Br)(Br)=O UXCDUFKZSUBXGM-UHFFFAOYSA-N 0.000 description 2
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CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical group C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 2
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QNMBSXGYAQZCTN-UHFFFAOYSA-N thiophen-3-ylboronic acid Chemical compound OB(O)C=1C=CSC=1 QNMBSXGYAQZCTN-UHFFFAOYSA-N 0.000 description 2
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TXMPGKJPXUFFPP-IBGZPJMESA-N ethyl (2s)-3-(4-hydroxyphenyl)-2-methyl-2-(4-methylphenoxy)propanoate Chemical compound C([C@@](C)(C(=O)OCC)OC=1C=CC(C)=CC=1)C1=CC=C(O)C=C1 TXMPGKJPXUFFPP-IBGZPJMESA-N 0.000 description 1
SLUUHAFCXRVNPS-UHFFFAOYSA-N ethyl 2-(2-methylphenoxy)propanoate Chemical compound CCOC(=O)C(C)OC1=CC=CC=C1C SLUUHAFCXRVNPS-UHFFFAOYSA-N 0.000 description 1
WMDVYBJHBYLFQU-UHFFFAOYSA-N ethyl 2-(3-bromophenoxy)-3-[4-[2-(2-cyclohexyl-5-methyl-1,3-oxazol-4-yl)ethoxy]phenyl]-2-methylpropanoate Chemical compound C=1C=CC(Br)=CC=1OC(C)(C(=O)OCC)CC(C=C1)=CC=C1OCCC(=C(O1)C)N=C1C1CCCCC1 WMDVYBJHBYLFQU-UHFFFAOYSA-N 0.000 description 1
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LGLVOSWWDSOCPG-UHFFFAOYSA-N ethyl 2-(4-methoxyphenoxy)-2-methyl-3-[4-[2-(5-methyl-2-thiophen-2-yl-1,3-oxazol-4-yl)ethoxy]phenyl]propanoate Chemical compound C=1C=C(OC)C=CC=1OC(C)(C(=O)OCC)CC(C=C1)=CC=C1OCCC(=C(O1)C)N=C1C1=CC=CS1 LGLVOSWWDSOCPG-UHFFFAOYSA-N 0.000 description 1
BKRNNVAVAGZOJU-UHFFFAOYSA-N ethyl 2-(4-tert-butylphenoxy)-2-methyl-3-(4-phenylmethoxyphenyl)-3-(2,2,2-trifluoroacetyl)oxypropanoate Chemical compound C=1C=C(OCC=2C=CC=CC=2)C=CC=1C(OC(=O)C(F)(F)F)C(C)(C(=O)OCC)OC1=CC=C(C(C)(C)C)C=C1 BKRNNVAVAGZOJU-UHFFFAOYSA-N 0.000 description 1
TYLZUBXZNIFQBI-UHFFFAOYSA-N ethyl 2-(4-tert-butylphenoxy)-3-hydroxy-2-methyl-3-(4-phenylmethoxyphenyl)propanoate Chemical compound C=1C=C(OCC=2C=CC=CC=2)C=CC=1C(O)C(C)(C(=O)OCC)OC1=CC=C(C(C)(C)C)C=C1 TYLZUBXZNIFQBI-UHFFFAOYSA-N 0.000 description 1
VGBZYLBDLXGDJR-UHFFFAOYSA-N ethyl 2-(4-tert-butylphenoxy)propanoate Chemical compound CCOC(=O)C(C)OC1=CC=C(C(C)(C)C)C=C1 VGBZYLBDLXGDJR-UHFFFAOYSA-N 0.000 description 1
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LSFYVKILZUSUGD-UHFFFAOYSA-N ethyl 2-methyl-3-[4-[2-[5-methyl-2-(2-phenylethyl)-1,3-oxazol-4-yl]ethoxy]phenyl]-2-phenoxypropanoate Chemical compound C=1C=CC=CC=1OC(C)(C(=O)OCC)CC(C=C1)=CC=C1OCCC(=C(O1)C)N=C1CCC1=CC=CC=C1 LSFYVKILZUSUGD-UHFFFAOYSA-N 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
- 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
- A61P3/04—Anorexiants; Antiobesity agents
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/04—Antihaemorrhagics; Procoagulants; Haemostatic agents; Antifibrinolytic agents
- 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
- 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
- A61P9/12—Antihypertensives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/32—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings

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SK187-2003A 2000-08-23 2001-08-23 Oxazolyl-arylpropionic acid derivatives and their use as PPAR agonists SK1872003A3 (en)

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 (1)

Publication Number	Publication Date
SK1872003A3 true SK1872003A3 (en)	2003-07-01

Family

ID=22852309

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK187-2003A SK1872003A3 (en)	2000-08-23	2001-08-23	Oxazolyl-arylpropionic acid derivatives and their use as PPAR agonists

Country Status (26)

Country	Link
US (2)	US6930120B2 (es)
EP (1)	EP1313716B1 (es)
JP (1)	JP2004506721A (es)
KR (1)	KR20030027054A (es)
CN (1)	CN1471517A (es)
AT (1)	ATE361283T1 (es)
AU (1)	AU2001284659A1 (es)
BR (1)	BR0113409A (es)
CA (1)	CA2418104A1 (es)
CY (1)	CY1107679T1 (es)
CZ (1)	CZ2003482A3 (es)
DE (1)	DE60128239T2 (es)
DK (1)	DK1313716T3 (es)
EA (1)	EA200300286A1 (es)
EC (1)	ECSP034504A (es)
ES (1)	ES2286137T3 (es)
HU (1)	HUP0300857A3 (es)
IL (1)	IL154110A0 (es)
MX (1)	MXPA03001558A (es)
NO (1)	NO20030729L (es)
NZ (1)	NZ523804A (es)
PL (1)	PL360744A1 (es)
PT (1)	PT1313716E (es)
SK (1)	SK1872003A3 (es)
WO (1)	WO2002016331A1 (es)
ZA (1)	ZA200300570B (es)

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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

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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

Also Published As

Publication number	Publication date
ES2286137T3 (es)	2007-12-01
CZ2003482A3 (cs)	2003-05-14
BR0113409A (pt)	2003-07-01
EP1313716B1 (en)	2007-05-02
HUP0300857A3 (en)	2007-03-28
IL154110A0 (en)	2003-07-31
US20050245584A1 (en)	2005-11-03
US6930120B2 (en)	2005-08-16
CY1107679T1 (el)	2013-04-18
NO20030729L (no)	2003-04-02
ECSP034504A (es)	2003-04-25
KR20030027054A (ko)	2003-04-03
DE60128239D1 (de)	2007-06-14
JP2004506721A (ja)	2004-03-04
ZA200300570B (en)	2004-04-21
AU2001284659A1 (en)	2002-03-04
HUP0300857A2 (hu)	2003-10-28
DE60128239T2 (de)	2008-01-10
NZ523804A (en)	2004-09-24
NO20030729D0 (no)	2003-02-14
US20040097590A1 (en)	2004-05-20
MXPA03001558A (es)	2003-06-06
US7345070B2 (en)	2008-03-18
CN1471517A (zh)	2004-01-28
ATE361283T1 (de)	2007-05-15
PT1313716E (pt)	2007-07-11
DK1313716T3 (da)	2007-08-27
EA200300286A1 (ru)	2003-08-28
WO2002016331A1 (en)	2002-02-28
EP1313716A1 (en)	2003-05-28
PL360744A1 (en)	2004-09-20
CA2418104A1 (en)	2002-02-28

Legal Events

Date	Code	Title	Description
2011-06-06	FC9A	Refused patent application

Publication	Publication Date	Title
US7282501B2 (en)	2007-10-16	Modulators of peroxisome proliferator activated receptors (PPAR)
ES2288982T3 (es)	2008-02-01	Derivados de acido oxazolil-ariloxiacetico y su uso como agonistas ppar.
US6825222B2 (en)	2004-11-30	Modulators of peroxisome proliferator activated receptors
ES2286137T3 (es)	2007-12-01	Derivados de acido oxazolil-arilpropionico y su uso como agonistas de ppar.
DE60131001T2 (de)	2008-07-17	Oxazolylarylpropionsäure derivate und ihre verwendung als ppar agonisten
EP1687299A1 (en)	2006-08-09	Heterocyclic compounds as modulators of peroxisome proliferator activated receptors, useful for the treamtment and/or prevention of disorders modulated by a ppar
AU2002316105A1 (en)	2002-12-23	Modulators of peroxisome proliferator activated receptors (PPAR)