WO2003059884A1 - Modulators of lxr - Google Patents
Modulators of lxr Download PDFInfo
- Publication number
- WO2003059884A1 WO2003059884A1 PCT/US2002/041306 US0241306W WO03059884A1 WO 2003059884 A1 WO2003059884 A1 WO 2003059884A1 US 0241306 W US0241306 W US 0241306W WO 03059884 A1 WO03059884 A1 WO 03059884A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- substituted
- unsubstituted
- alkyl
- aryl
- phenyl
- Prior art date
Links
- 0 CC1(*)C=CC(C(N(C[Al])C2=O)=C(*)C(C(F)(F)F)=C2C#N)=CC=C1 Chemical compound CC1(*)C=CC(C(N(C[Al])C2=O)=C(*)C(C(F)(F)F)=C2C#N)=CC=C1 0.000 description 19
- CFQXJPQXCBNNGN-UHFFFAOYSA-N CC(C=C(c(cc1)ccc1Cl)N(C1=O)N=C2CCCCC2)=C1C#N Chemical compound CC(C=C(c(cc1)ccc1Cl)N(C1=O)N=C2CCCCC2)=C1C#N CFQXJPQXCBNNGN-UHFFFAOYSA-N 0.000 description 1
- QTMKNCZDUKCLAQ-UHFFFAOYSA-O CC(CC(c1ccccc1)=C1C#N)(c2ccccc2)[NH2+]C1=O Chemical compound CC(CC(c1ccccc1)=C1C#N)(c2ccccc2)[NH2+]C1=O QTMKNCZDUKCLAQ-UHFFFAOYSA-O 0.000 description 1
- JCBAVTRNIZTODS-UHFFFAOYSA-N CC(CC1)CCC1=NN(C(c1ccccc1)=CC(C(F)(F)F)=C1C#N)C1=O Chemical compound CC(CC1)CCC1=NN(C(c1ccccc1)=CC(C(F)(F)F)=C1C#N)C1=O JCBAVTRNIZTODS-UHFFFAOYSA-N 0.000 description 1
- SXCDFHMRBSIALG-UHFFFAOYSA-O CC(CCC1)CC1=N[NH+](C(c1ccccc1)=CC(C(F)(F)F)=C1C#N)C1=O Chemical compound CC(CCC1)CC1=N[NH+](C(c1ccccc1)=CC(C(F)(F)F)=C1C#N)C1=O SXCDFHMRBSIALG-UHFFFAOYSA-O 0.000 description 1
- OGQMCYLHGWWGDQ-UHFFFAOYSA-N CC(c1ccc(CN(C(c2ccccc2)=CC(C(F)(F)F)=C2C#N)C2=O)cc1)=O Chemical compound CC(c1ccc(CN(C(c2ccccc2)=CC(C(F)(F)F)=C2C#N)C2=O)cc1)=O OGQMCYLHGWWGDQ-UHFFFAOYSA-N 0.000 description 1
- VQRLELPDQDHRRW-UHFFFAOYSA-N CC1(C)OC(CN(C(c2ccccc2)=CC(C(F)(F)F)=C2C#N)C2=O)CO1 Chemical compound CC1(C)OC(CN(C(c2ccccc2)=CC(C(F)(F)F)=C2C#N)C2=O)CO1 VQRLELPDQDHRRW-UHFFFAOYSA-N 0.000 description 1
- JYSDPCJCMLAIEC-UHFFFAOYSA-N CCC(CC1)CCC1=NN(C(c1ccc[s]1)=CC(C(F)(F)F)=C1C#N)C1=O Chemical compound CCC(CC1)CCC1=NN(C(c1ccc[s]1)=CC(C(F)(F)F)=C1C#N)C1=O JYSDPCJCMLAIEC-UHFFFAOYSA-N 0.000 description 1
- QFLIIQVXDWNISE-UHFFFAOYSA-N CCCCCCCCOCc1ccc(CN(C(c2cc(C)ccc2)=CC(C(F)(F)F)=C2C#N)C2=O)cc1 Chemical compound CCCCCCCCOCc1ccc(CN(C(c2cc(C)ccc2)=CC(C(F)(F)F)=C2C#N)C2=O)cc1 QFLIIQVXDWNISE-UHFFFAOYSA-N 0.000 description 1
- FQYYWARVBWGGQF-UHFFFAOYSA-N CCN(CC)C(c1cccc(C(N(Cc2ccccc2)C2=O)=CC(C(F)(F)F)=C2C#N)c1)=O Chemical compound CCN(CC)C(c1cccc(C(N(Cc2ccccc2)C2=O)=CC(C(F)(F)F)=C2C#N)c1)=O FQYYWARVBWGGQF-UHFFFAOYSA-N 0.000 description 1
- PSUPUEVNANRBIR-UHFFFAOYSA-N CCOC(c1cc(Oc(cc2)ccc2C(N(Cc2ccc(C)cc2C)C2=O)=CC(C(F)(F)F)=C2C#N)ccc1)=O Chemical compound CCOC(c1cc(Oc(cc2)ccc2C(N(Cc2ccc(C)cc2C)C2=O)=CC(C(F)(F)F)=C2C#N)ccc1)=O PSUPUEVNANRBIR-UHFFFAOYSA-N 0.000 description 1
- XTJJFXUGNHLSAU-UHFFFAOYSA-N CCc1cc(C(N(Cc2ccc(C)c(C)c2)C2=O)=CC(C(F)(F)F)=C2C#N)ccc1 Chemical compound CCc1cc(C(N(Cc2ccc(C)c(C)c2)C2=O)=CC(C(F)(F)F)=C2C#N)ccc1 XTJJFXUGNHLSAU-UHFFFAOYSA-N 0.000 description 1
- XULCZPJTEFIMLV-UHFFFAOYSA-N CCc1ccc(CN(C(c2cccc(C)c2)=CC(C(F)(F)F)=C2C#N)C2=O)cc1 Chemical compound CCc1ccc(CN(C(c2cccc(C)c2)=CC(C(F)(F)F)=C2C#N)C2=O)cc1 XULCZPJTEFIMLV-UHFFFAOYSA-N 0.000 description 1
- WEVHKXLJRAWCMU-UHFFFAOYSA-N COC(c1ccc(COc2cc(C(N(Cc3ccccc3)C3=O)=CC(C(F)(F)F)=C3C#N)ccc2)cc1)=O Chemical compound COC(c1ccc(COc2cc(C(N(Cc3ccccc3)C3=O)=CC(C(F)(F)F)=C3C#N)ccc2)cc1)=O WEVHKXLJRAWCMU-UHFFFAOYSA-N 0.000 description 1
- KVKFQVOBWASLDZ-UHFFFAOYSA-O COc(cc1)ccc1C([NH2+]C1=[O]C(CCCC2)C2=N)=CC(C(F)(F)F)=C1C#N Chemical compound COc(cc1)ccc1C([NH2+]C1=[O]C(CCCC2)C2=N)=CC(C(F)(F)F)=C1C#N KVKFQVOBWASLDZ-UHFFFAOYSA-O 0.000 description 1
- GUFWHQBUCBMLFM-UHFFFAOYSA-N Cc1cc(C(N(CC(C2C=CC=C3)C23Cl)C2=O)=CC(C(F)(F)F)=C2C#N)ccc1 Chemical compound Cc1cc(C(N(CC(C2C=CC=C3)C23Cl)C2=O)=CC(C(F)(F)F)=C2C#N)ccc1 GUFWHQBUCBMLFM-UHFFFAOYSA-N 0.000 description 1
- HTHAKHSOOWRNTH-UHFFFAOYSA-N Cc1cc(C(N(Cc2c[s]c(-c3ccccc3)n2)C2=O)=CC(C(F)(F)F)=C2C#N)cc(C)c1 Chemical compound Cc1cc(C(N(Cc2c[s]c(-c3ccccc3)n2)C2=O)=CC(C(F)(F)F)=C2C#N)cc(C)c1 HTHAKHSOOWRNTH-UHFFFAOYSA-N 0.000 description 1
- DIRKRRGXUQFGLX-UHFFFAOYSA-N Cc1cc(C(N(Cc2ccc(C(F)(F)F)cc2)C2=O)=CC(C(F)(F)F)=C2C#N)ccc1 Chemical compound Cc1cc(C(N(Cc2ccc(C(F)(F)F)cc2)C2=O)=CC(C(F)(F)F)=C2C#N)ccc1 DIRKRRGXUQFGLX-UHFFFAOYSA-N 0.000 description 1
- IZASSLPJAYHNNA-UHFFFAOYSA-N Cc1cc(C(N(Cc2ccc(COC)cc2)C2=O)=CC(C(F)(F)F)=C2C#N)ccc1 Chemical compound Cc1cc(C(N(Cc2ccc(COC)cc2)C2=O)=CC(C(F)(F)F)=C2C#N)ccc1 IZASSLPJAYHNNA-UHFFFAOYSA-N 0.000 description 1
- SXXIGBAVPSDTTG-UHFFFAOYSA-N Cc1cc(C(N(Cc2ccccc2)C2=O)=CC(C(F)(F)F)=C2C#N)ccc1 Chemical compound Cc1cc(C(N(Cc2ccccc2)C2=O)=CC(C(F)(F)F)=C2C#N)ccc1 SXXIGBAVPSDTTG-UHFFFAOYSA-N 0.000 description 1
- FOTDLWCKHWLEBR-UHFFFAOYSA-N Cc1cc(CN(C(c(cc2)ccc2Oc2ccccc2)=CC(C(C(F)(F)F)(F)F)=C2C#N)C2=O)ccc1 Chemical compound Cc1cc(CN(C(c(cc2)ccc2Oc2ccccc2)=CC(C(C(F)(F)F)(F)F)=C2C#N)C2=O)ccc1 FOTDLWCKHWLEBR-UHFFFAOYSA-N 0.000 description 1
- NOOVSAFOSUSHCK-UHFFFAOYSA-N Cc1ccc(C)c(CN(C(c2ccccc2)=CC(C(F)(F)F)=C2C#N)C2=O)c1 Chemical compound Cc1ccc(C)c(CN(C(c2ccccc2)=CC(C(F)(F)F)=C2C#N)C2=O)c1 NOOVSAFOSUSHCK-UHFFFAOYSA-N 0.000 description 1
- SDVRDDUILYXROT-UHFFFAOYSA-N Cc1ccc(CN(C(c(cc2)ccc2OC2OCCCC2)=CC(C(F)(F)F)=C2C#N)C2=O)c(C)c1 Chemical compound Cc1ccc(CN(C(c(cc2)ccc2OC2OCCCC2)=CC(C(F)(F)F)=C2C#N)C2=O)c(C)c1 SDVRDDUILYXROT-UHFFFAOYSA-N 0.000 description 1
- MHLPCRFKFJSFDZ-UHFFFAOYSA-N Cc1ccc(CN(C(c(cc2)ccc2Oc(cc2)ccc2Br)=CC(C(F)(F)F)=C2C#N)C2=O)c(C)c1 Chemical compound Cc1ccc(CN(C(c(cc2)ccc2Oc(cc2)ccc2Br)=CC(C(F)(F)F)=C2C#N)C2=O)c(C)c1 MHLPCRFKFJSFDZ-UHFFFAOYSA-N 0.000 description 1
- ARNKWYXFZXTVOG-UHFFFAOYSA-N Cc1ccc(CN(C(c(cc2)ccc2Oc2cc(C)cc(C)c2)=CC(C(F)(F)F)=C2C#N)C2=O)c(C)c1 Chemical compound Cc1ccc(CN(C(c(cc2)ccc2Oc2cc(C)cc(C)c2)=CC(C(F)(F)F)=C2C#N)C2=O)c(C)c1 ARNKWYXFZXTVOG-UHFFFAOYSA-N 0.000 description 1
- QUGOVALGZHZZHQ-UHFFFAOYSA-N Cc1ccc(CN(C(c(cc2)ccc2Oc2cccc(C(O)=O)c2)=CC(C(F)(F)F)=C2C#N)C2=O)c(C=[IH])c1 Chemical compound Cc1ccc(CN(C(c(cc2)ccc2Oc2cccc(C(O)=O)c2)=CC(C(F)(F)F)=C2C#N)C2=O)c(C=[IH])c1 QUGOVALGZHZZHQ-UHFFFAOYSA-N 0.000 description 1
- VLPDWGCFLQALLA-UHFFFAOYSA-N Cc1ccc(CN(C(c2ncc[s]2)=CC(C(C(F)(F)F)(F)F)=C2C#N)C2=O)c(C)c1 Chemical compound Cc1ccc(CN(C(c2ncc[s]2)=CC(C(C(F)(F)F)(F)F)=C2C#N)C2=O)c(C)c1 VLPDWGCFLQALLA-UHFFFAOYSA-N 0.000 description 1
- TVOMCJNVEIKQIP-UHFFFAOYSA-N Cc1ccc(CNC(CC#N)=O)c(C)c1 Chemical compound Cc1ccc(CNC(CC#N)=O)c(C)c1 TVOMCJNVEIKQIP-UHFFFAOYSA-N 0.000 description 1
- BNXPCVGBSLTWQU-UHFFFAOYSA-N Cc1cccc(C(N(Cc2cccc(C(F)(F)F)c2)C2=O)=CC(C(F)(F)F)=C2C#N)c1 Chemical compound Cc1cccc(C(N(Cc2cccc(C(F)(F)F)c2)C2=O)=CC(C(F)(F)F)=C2C#N)c1 BNXPCVGBSLTWQU-UHFFFAOYSA-N 0.000 description 1
- GCVZBEDFQNFAPW-UHFFFAOYSA-O N#CC(C1=O)=C(C(F)(F)F)C=C(c2ccccc2)[NH+]1N=C(CCCC1)C1c1ccccc1 Chemical compound N#CC(C1=O)=C(C(F)(F)F)C=C(c2ccccc2)[NH+]1N=C(CCCC1)C1c1ccccc1 GCVZBEDFQNFAPW-UHFFFAOYSA-O 0.000 description 1
- NYXQKHZBWWEXAY-UHFFFAOYSA-N N#CC1=C(C(F)(F)F)C=C(c2ccccc2)N(Cc2ccc(C(F)(F)F)cc2)C1=O Chemical compound N#CC1=C(C(F)(F)F)C=C(c2ccccc2)N(Cc2ccc(C(F)(F)F)cc2)C1=O NYXQKHZBWWEXAY-UHFFFAOYSA-N 0.000 description 1
- UZJNCSFBCFBIEX-UHFFFAOYSA-N N#CC1=C(C(F)(F)F)C=C(c2ccccc2)N(Cc2ccccc2)C1=S Chemical compound N#CC1=C(C(F)(F)F)C=C(c2ccccc2)N(Cc2ccccc2)C1=S UZJNCSFBCFBIEX-UHFFFAOYSA-N 0.000 description 1
- WKWBOZPKWLHXMR-UHFFFAOYSA-N N#CCC(NCCCc1ccccc1)=O Chemical compound N#CCC(NCCCc1ccccc1)=O WKWBOZPKWLHXMR-UHFFFAOYSA-N 0.000 description 1
- XBYXVCRXCIJINE-UHFFFAOYSA-N N#CCC(NCc(c(C=[IH])c1)ccc1Cl)=O Chemical compound N#CCC(NCc(c(C=[IH])c1)ccc1Cl)=O XBYXVCRXCIJINE-UHFFFAOYSA-N 0.000 description 1
- UKKHUKFEKBKULS-UHFFFAOYSA-N N#CCC(NCc(cc1)ccc1Cl)=O Chemical compound N#CCC(NCc(cc1)ccc1Cl)=O UKKHUKFEKBKULS-UHFFFAOYSA-N 0.000 description 1
- OBRPXZYTBBNYPA-UHFFFAOYSA-N N#CCC(NCc1ccccc1Cl)=O Chemical compound N#CCC(NCc1ccccc1Cl)=O OBRPXZYTBBNYPA-UHFFFAOYSA-N 0.000 description 1
- XCTQPMCULSZKLT-UHFFFAOYSA-N N#CCC(Nc1ccccc1)=O Chemical compound N#CCC(Nc1ccccc1)=O XCTQPMCULSZKLT-UHFFFAOYSA-N 0.000 description 1
- NALMTAGQHWNRBI-UHFFFAOYSA-O Nc(cccc1)c1[O]=C(CC#N)[NH3+] Chemical compound Nc(cccc1)c1[O]=C(CC#N)[NH3+] NALMTAGQHWNRBI-UHFFFAOYSA-O 0.000 description 1
- KZOWVHBIEBBVQS-UHFFFAOYSA-N O=C(Cc1ccccc1)NCC1=C(C(F)(F)F)C=C(c2ccccc2)N(Cc2ccccc2)C1=O Chemical compound O=C(Cc1ccccc1)NCC1=C(C(F)(F)F)C=C(c2ccccc2)N(Cc2ccccc2)C1=O KZOWVHBIEBBVQS-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/84—Nitriles
- C07D213/85—Nitriles in position 3
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- C—CHEMISTRY; METALLURGY
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
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- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
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- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- 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
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- C07D417/00—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
- 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
- C07D417/04—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 directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—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
- 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
- C07D417/06—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 carbon chain containing only aliphatic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—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
- 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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EP02787071.6A EP1465869B1 (en) | 2001-12-21 | 2002-12-20 | Modulators of lxr |
AU2002351412A AU2002351412B2 (en) | 2001-12-21 | 2002-12-20 | Modulators of LXR |
JP2003559988A JP5082033B2 (ja) | 2001-12-21 | 2002-12-20 | Lxrのモジュレーター |
CA002469435A CA2469435A1 (en) | 2001-12-21 | 2002-12-20 | Modulators of lxr |
ES02787071T ES2421511T3 (es) | 2001-12-21 | 2002-12-20 | Moduladores de LXR |
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US34270701P | 2001-12-21 | 2001-12-21 | |
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CA2469435A1 (en) | 2003-07-24 |
JP5082033B2 (ja) | 2012-11-28 |
JP2005536450A (ja) | 2005-12-02 |
US20030181420A1 (en) | 2003-09-25 |
AU2002351412A1 (en) | 2003-07-30 |
EP1465869A4 (en) | 2005-12-28 |
EP1465869B1 (en) | 2013-05-15 |
ES2421511T3 (es) | 2013-09-03 |
EP1465869A1 (en) | 2004-10-13 |
AU2002351412B2 (en) | 2010-05-20 |
US7998986B2 (en) | 2011-08-16 |
JP2010280732A (ja) | 2010-12-16 |
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