EA008798B1 - НОВЫЕ БЕНЗАМИДЫ В КАЧЕСТВЕ PPARγ МОДУЛЯТОРОВ - Google Patents
НОВЫЕ БЕНЗАМИДЫ В КАЧЕСТВЕ PPARγ МОДУЛЯТОРОВ Download PDFInfo
- Publication number
- EA008798B1 EA008798B1 EA200600023A EA200600023A EA008798B1 EA 008798 B1 EA008798 B1 EA 008798B1 EA 200600023 A EA200600023 A EA 200600023A EA 200600023 A EA200600023 A EA 200600023A EA 008798 B1 EA008798 B1 EA 008798B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- benzoylamino
- optionally substituted
- propionic acid
- alkyl
- benzyloxyphenyl
- Prior art date
Links
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- ZAENUMHSSYFQKM-UHFFFAOYSA-N ethyl 2-[[3-[2-(dibenzylamino)ethoxy]benzoyl]-[(4-phenoxyphenyl)methyl]amino]acetate Chemical compound C=1C=CC(OCCN(CC=2C=CC=CC=2)CC=2C=CC=CC=2)=CC=1C(=O)N(CC(=O)OCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 ZAENUMHSSYFQKM-UHFFFAOYSA-N 0.000 description 1
- OVTMRQMBPXPPMI-UHFFFAOYSA-N ethyl 2-[[4-[(3-phenylmethoxyphenyl)methoxy]benzoyl]-[(3-phenylmethoxyphenyl)methyl]amino]acetate Chemical compound C=1C=C(OCC=2C=C(OCC=3C=CC=CC=3)C=CC=2)C=CC=1C(=O)N(CC(=O)OCC)CC(C=1)=CC=CC=1OCC1=CC=CC=C1 OVTMRQMBPXPPMI-UHFFFAOYSA-N 0.000 description 1
- ROABVPLACICSLF-UHFFFAOYSA-N ethyl 2-[[4-[2-(dibenzylamino)ethoxy]benzoyl]-[(3-phenoxyphenyl)methyl]amino]acetate Chemical compound C=1C=C(OCCN(CC=2C=CC=CC=2)CC=2C=CC=CC=2)C=CC=1C(=O)N(CC(=O)OCC)CC(C=1)=CC=CC=1OC1=CC=CC=C1 ROABVPLACICSLF-UHFFFAOYSA-N 0.000 description 1
- QLYCZRWZOVSPAF-UHFFFAOYSA-N ethyl 2-[[4-[2-(dibenzylamino)ethoxy]benzoyl]-[(4-phenylmethoxyphenyl)methyl]amino]acetate Chemical compound C=1C=C(OCCN(CC=2C=CC=CC=2)CC=2C=CC=CC=2)C=CC=1C(=O)N(CC(=O)OCC)CC(C=C1)=CC=C1OCC1=CC=CC=C1 QLYCZRWZOVSPAF-UHFFFAOYSA-N 0.000 description 1
- ULMPKGWUJCZZQN-UHFFFAOYSA-N ethyl 3-[(4-phenylmethoxybenzoyl)-[(3-phenylmethoxyphenyl)methyl]amino]propanoate Chemical compound C=1C=C(OCC=2C=CC=CC=2)C=CC=1C(=O)N(CCC(=O)OCC)CC(C=1)=CC=CC=1OCC1=CC=CC=C1 ULMPKGWUJCZZQN-UHFFFAOYSA-N 0.000 description 1
- HFHDIYOUJRJKGV-UHFFFAOYSA-N ethyl 3-[[3-[(3-phenylmethoxyphenyl)methoxy]benzoyl]-[(3-phenylmethoxyphenyl)methyl]amino]propanoate Chemical compound C=1C=CC(OCC=2C=C(OCC=3C=CC=CC=3)C=CC=2)=CC=1C(=O)N(CCC(=O)OCC)CC(C=1)=CC=CC=1OCC1=CC=CC=C1 HFHDIYOUJRJKGV-UHFFFAOYSA-N 0.000 description 1
- FRNRJKYSGLADSG-UHFFFAOYSA-N ethyl 3-[[3-[2-(3-methylquinoxalin-2-yl)oxyethoxy]benzoyl]-[(3-phenylmethoxyphenyl)methyl]amino]propanoate Chemical compound C=1C=CC(OCCOC=2C(=NC3=CC=CC=C3N=2)C)=CC=1C(=O)N(CCC(=O)OCC)CC(C=1)=CC=CC=1OCC1=CC=CC=C1 FRNRJKYSGLADSG-UHFFFAOYSA-N 0.000 description 1
- JDSVRNRDIMCWPB-UHFFFAOYSA-N ethyl 3-[[4-[(3-phenylmethoxyphenyl)methoxy]benzoyl]-[(3-phenylmethoxyphenyl)methyl]amino]propanoate Chemical compound C=1C=C(OCC=2C=C(OCC=3C=CC=CC=3)C=CC=2)C=CC=1C(=O)N(CCC(=O)OCC)CC(C=1)=CC=CC=1OCC1=CC=CC=C1 JDSVRNRDIMCWPB-UHFFFAOYSA-N 0.000 description 1
- FMMIDKLHWFWJRV-UHFFFAOYSA-N ethyl 3-[[4-[(3-phenylmethoxyphenyl)methoxy]benzoyl]-[(4-phenylmethoxyphenyl)methyl]amino]propanoate Chemical compound C=1C=C(OCC=2C=C(OCC=3C=CC=CC=3)C=CC=2)C=CC=1C(=O)N(CCC(=O)OCC)CC(C=C1)=CC=C1OCC1=CC=CC=C1 FMMIDKLHWFWJRV-UHFFFAOYSA-N 0.000 description 1
- PIDQSFMQEQGVLD-UHFFFAOYSA-N ethyl 3-[[4-[2-(3-methylquinoxalin-2-yl)oxyethoxy]benzoyl]-[(3-phenylmethoxyphenyl)methyl]amino]propanoate Chemical compound C=1C=C(OCCOC=2C(=NC3=CC=CC=C3N=2)C)C=CC=1C(=O)N(CCC(=O)OCC)CC(C=1)=CC=CC=1OCC1=CC=CC=C1 PIDQSFMQEQGVLD-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 1
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- 150000002333 glycines Chemical class 0.000 description 1
- 230000013632 homeostatic process Effects 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 201000001421 hyperglycemia Diseases 0.000 description 1
- 206010020718 hyperplasia Diseases 0.000 description 1
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- 230000028709 inflammatory response Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229940125396 insulin Drugs 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 201000002313 intestinal cancer Diseases 0.000 description 1
- 210000002510 keratinocyte Anatomy 0.000 description 1
- 235000020778 linoleic acid Nutrition 0.000 description 1
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000005567 liquid scintillation counting Methods 0.000 description 1
- 210000005228 liver tissue Anatomy 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 108020004999 messenger RNA Proteins 0.000 description 1
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- 229910021645 metal ion Inorganic materials 0.000 description 1
- SRWPXCNJACHZDW-UHFFFAOYSA-N methyl 2-[[3-[(4-butylphenyl)methoxy]benzoyl]-[(3-phenylmethoxyphenyl)methyl]amino]acetate Chemical compound C1=CC(CCCC)=CC=C1COC1=CC=CC(C(=O)N(CC(=O)OC)CC=2C=C(OCC=3C=CC=CC=3)C=CC=2)=C1 SRWPXCNJACHZDW-UHFFFAOYSA-N 0.000 description 1
- ZUDPBZWCUKFNFZ-UHFFFAOYSA-N methyl 2-[[3-[(4-phenylmethoxyphenyl)methoxy]benzoyl]-[(3-phenylmethoxyphenyl)methyl]amino]acetate Chemical compound COC(CN(C(C1=CC(=CC=C1)OCC1=CC=C(C=C1)OCC1=CC=CC=C1)=O)CC1=CC(=CC=C1)OCC1=CC=CC=C1)=O ZUDPBZWCUKFNFZ-UHFFFAOYSA-N 0.000 description 1
- OGFVPMVNPIUNAF-UHFFFAOYSA-N methyl 2-[[3-[2-(dibenzylamino)ethoxy]benzoyl]amino]-3-(5-phenylmethoxy-1h-indol-3-yl)propanoate Chemical compound C=1C=CC(OCCN(CC=2C=CC=CC=2)CC=2C=CC=CC=2)=CC=1C(=O)NC(C(=O)OC)CC(C1=C2)=CNC1=CC=C2OCC1=CC=CC=C1 OGFVPMVNPIUNAF-UHFFFAOYSA-N 0.000 description 1
- YTDXIYLLILPBSX-UHFFFAOYSA-N methyl 2-[[3-[2-[benzyl(2-phenylethyl)amino]-2-oxoethoxy]benzoyl]amino]-3-(4-phenylmethoxyphenyl)propanoate Chemical compound COC(C(CC1=CC=C(C=C1)OCC1=CC=CC=C1)NC(C1=CC(=CC=C1)OCC(N(CCC1=CC=CC=C1)CC1=CC=CC=C1)=O)=O)=O YTDXIYLLILPBSX-UHFFFAOYSA-N 0.000 description 1
- VFGQCQIBSLOKAU-UHFFFAOYSA-N methyl 2-[[4-[(2-methylquinolin-4-yl)methoxy]benzoyl]amino]-2-(oxan-4-yl)acetate Chemical compound C=1C=C(OCC=2C3=CC=CC=C3N=C(C)C=2)C=CC=1C(=O)NC(C(=O)OC)C1CCOCC1 VFGQCQIBSLOKAU-UHFFFAOYSA-N 0.000 description 1
- WHJJXHZUYNXWIK-UHFFFAOYSA-N methyl 2-[[4-[(4-butylphenyl)methoxy]benzoyl]-[(3-phenylmethoxyphenyl)methyl]amino]acetate Chemical compound C1=CC(CCCC)=CC=C1COC1=CC=C(C(=O)N(CC(=O)OC)CC=2C=C(OCC=3C=CC=CC=3)C=CC=2)C=C1 WHJJXHZUYNXWIK-UHFFFAOYSA-N 0.000 description 1
- VJKKEJAVZKMMDW-UHFFFAOYSA-N methyl 2-[[4-[(4-butylphenyl)methoxy]benzoyl]-[(4-phenylmethoxyphenyl)methyl]amino]acetate Chemical compound C1=CC(CCCC)=CC=C1COC1=CC=C(C(=O)N(CC(=O)OC)CC=2C=CC(OCC=3C=CC=CC=3)=CC=2)C=C1 VJKKEJAVZKMMDW-UHFFFAOYSA-N 0.000 description 1
- CFKVYAHTXZNWKH-UHFFFAOYSA-N methyl 2-[[4-[2-(dibenzylamino)-2-oxoethoxy]benzoyl]amino]-3-(4-phenylmethoxyphenyl)propanoate Chemical compound C=1C=C(OCC(=O)N(CC=2C=CC=CC=2)CC=2C=CC=CC=2)C=CC=1C(=O)NC(C(=O)OC)CC(C=C1)=CC=C1OCC1=CC=CC=C1 CFKVYAHTXZNWKH-UHFFFAOYSA-N 0.000 description 1
- FINSFSWZVURYNM-UHFFFAOYSA-N methyl 2-[[4-[2-(dibenzylamino)ethoxy]benzoyl]amino]-3-(1-methylindol-3-yl)propanoate Chemical compound C=1N(C)C2=CC=CC=C2C=1CC(C(=O)OC)NC(=O)C(C=C1)=CC=C1OCCN(CC=1C=CC=CC=1)CC1=CC=CC=C1 FINSFSWZVURYNM-UHFFFAOYSA-N 0.000 description 1
- BBYNFLOSUXDKEK-UHFFFAOYSA-N methyl 2-[[4-[2-(dibenzylamino)ethoxy]benzoyl]amino]-3-(5-phenylmethoxy-1h-indol-3-yl)propanoate Chemical compound C=1C=C(OCCN(CC=2C=CC=CC=2)CC=2C=CC=CC=2)C=CC=1C(=O)NC(C(=O)OC)CC(C1=C2)=CNC1=CC=C2OCC1=CC=CC=C1 BBYNFLOSUXDKEK-UHFFFAOYSA-N 0.000 description 1
- QNMUVUIZUVEBPS-UHFFFAOYSA-N methyl 2-[[4-[2-(n-(3-methoxyphenyl)anilino)-2-oxoethoxy]benzoyl]amino]-3-(4-phenylmethoxyphenyl)propanoate Chemical compound C=1C=C(OCC(=O)N(C=2C=CC=CC=2)C=2C=C(OC)C=CC=2)C=CC=1C(=O)NC(C(=O)OC)CC(C=C1)=CC=C1OCC1=CC=CC=C1 QNMUVUIZUVEBPS-UHFFFAOYSA-N 0.000 description 1
- RDDZXKZLNMYUJO-UHFFFAOYSA-N methyl 2-[[4-[2-(n-benzylanilino)-2-oxoethoxy]benzoyl]amino]-3-(4-phenylmethoxyphenyl)propanoate Chemical compound C=1C=C(OCC(=O)N(CC=2C=CC=CC=2)C=2C=CC=CC=2)C=CC=1C(=O)NC(C(=O)OC)CC(C=C1)=CC=C1OCC1=CC=CC=C1 RDDZXKZLNMYUJO-UHFFFAOYSA-N 0.000 description 1
- HSQCOTOHFVZWFZ-UHFFFAOYSA-N methyl 2-[[4-[2-(n-cyclohexylanilino)-2-oxoethoxy]benzoyl]amino]-3-(4-phenylmethoxyphenyl)propanoate Chemical compound C=1C=C(OCC(=O)N(C2CCCCC2)C=2C=CC=CC=2)C=CC=1C(=O)NC(C(=O)OC)CC(C=C1)=CC=C1OCC1=CC=CC=C1 HSQCOTOHFVZWFZ-UHFFFAOYSA-N 0.000 description 1
- UUWRILBNTDRPBY-UHFFFAOYSA-N methyl 2-[[4-[2-oxo-2-(n-phenylanilino)ethoxy]benzoyl]amino]-3-(4-phenylmethoxyphenyl)propanoate Chemical compound C=1C=C(OCC(=O)N(C=2C=CC=CC=2)C=2C=CC=CC=2)C=CC=1C(=O)NC(C(=O)OC)CC(C=C1)=CC=C1OCC1=CC=CC=C1 UUWRILBNTDRPBY-UHFFFAOYSA-N 0.000 description 1
- WLJHVKATIUSKIM-UHFFFAOYSA-N methyl 2-[thiophen-2-yl-[3-(2-thiophen-2-ylsulfanylethoxy)benzoyl]amino]acetate Chemical compound C=1C=CSC=1N(CC(=O)OC)C(=O)C(C=1)=CC=CC=1OCCSC1=CC=CS1 WLJHVKATIUSKIM-UHFFFAOYSA-N 0.000 description 1
- ZAQUSCMBWBLJLJ-UHFFFAOYSA-N methyl 2-[thiophen-3-ylmethyl-[3-(2-thiophen-2-ylsulfanylethoxy)benzoyl]amino]acetate Chemical compound COC(=O)CN(Cc1ccsc1)C(=O)c1cccc(OCCSc2cccs2)c1 ZAQUSCMBWBLJLJ-UHFFFAOYSA-N 0.000 description 1
- LOGMLLUWDQSQMG-UHFFFAOYSA-N methyl 3-(4-bromophenyl)-2-[[4-[(3-phenylmethoxyphenyl)methoxy]benzoyl]amino]propanoate Chemical compound C=1C=C(OCC=2C=C(OCC=3C=CC=CC=3)C=CC=2)C=CC=1C(=O)NC(C(=O)OC)CC1=CC=C(Br)C=C1 LOGMLLUWDQSQMG-UHFFFAOYSA-N 0.000 description 1
- ODWFBNKOTOMGBM-UHFFFAOYSA-N methyl 3-(4-fluorophenyl)-2-[[4-[(3-phenylmethoxyphenyl)methoxy]benzoyl]amino]propanoate Chemical compound C=1C=C(OCC=2C=C(OCC=3C=CC=CC=3)C=CC=2)C=CC=1C(=O)NC(C(=O)OC)CC1=CC=C(F)C=C1 ODWFBNKOTOMGBM-UHFFFAOYSA-N 0.000 description 1
- YJQKEMJLJQGZLO-UHFFFAOYSA-N methyl 3-[(4-tert-butylphenyl)methyl-[3-[2-(dibenzylamino)ethoxy]benzoyl]amino]propanoate Chemical compound C=1C=CC(OCCN(CC=2C=CC=CC=2)CC=2C=CC=CC=2)=CC=1C(=O)N(CCC(=O)OC)CC1=CC=C(C(C)(C)C)C=C1 YJQKEMJLJQGZLO-UHFFFAOYSA-N 0.000 description 1
- AEYPVQWBXNVTDV-UHFFFAOYSA-N methyl 3-[2-(3-methylquinoxalin-2-yl)oxyethoxy]benzoate Chemical compound COC(=O)C1=CC=CC(OCCOC=2C(=NC3=CC=CC=C3N=2)C)=C1 AEYPVQWBXNVTDV-UHFFFAOYSA-N 0.000 description 1
- SSTPMVDSHNSVCZ-UHFFFAOYSA-N methyl 3-[2-[benzyl-(2,2,2-trifluoroacetyl)amino]ethoxy]benzoate Chemical compound COC(=O)c1cccc(OCCN(Cc2ccccc2)C(=O)C(F)(F)F)c1 SSTPMVDSHNSVCZ-UHFFFAOYSA-N 0.000 description 1
- SGPLCNDUSSXFSW-UHFFFAOYSA-N methyl 3-[[3-[(4-butylphenyl)methoxy]benzoyl]-[(3-phenylmethoxyphenyl)methyl]amino]propanoate Chemical compound C1=CC(CCCC)=CC=C1COC1=CC=CC(C(=O)N(CCC(=O)OC)CC=2C=C(OCC=3C=CC=CC=3)C=CC=2)=C1 SGPLCNDUSSXFSW-UHFFFAOYSA-N 0.000 description 1
- NVHAUEZAIBWBKJ-UHFFFAOYSA-N methyl 3-[[3-[(4-phenylmethoxyphenyl)methoxy]benzoyl]-[(3-phenylmethoxyphenyl)methyl]amino]propanoate Chemical compound C=1C=CC(OCC=2C=CC(OCC=3C=CC=CC=3)=CC=2)=CC=1C(=O)N(CCC(=O)OC)CC(C=1)=CC=CC=1OCC1=CC=CC=C1 NVHAUEZAIBWBKJ-UHFFFAOYSA-N 0.000 description 1
- KZSCDRRNYAQNNV-UHFFFAOYSA-N methyl 3-[[3-[2-(dibenzylamino)ethoxy]benzoyl]-(naphthalen-2-ylmethyl)amino]propanoate Chemical compound C=1C=C2C=CC=CC2=CC=1CN(CCC(=O)OC)C(=O)C(C=1)=CC=CC=1OCCN(CC=1C=CC=CC=1)CC1=CC=CC=C1 KZSCDRRNYAQNNV-UHFFFAOYSA-N 0.000 description 1
- HTOFZUOCSUKVMW-UHFFFAOYSA-N methyl 3-[[4-[(4-butylphenyl)methoxy]benzoyl]-[(4-phenylmethoxyphenyl)methyl]amino]propanoate Chemical compound C1=CC(CCCC)=CC=C1COC1=CC=C(C(=O)N(CCC(=O)OC)CC=2C=CC(OCC=3C=CC=CC=3)=CC=2)C=C1 HTOFZUOCSUKVMW-UHFFFAOYSA-N 0.000 description 1
- UHFWPEQXZWFBKR-UHFFFAOYSA-N methyl 3-[[4-[2-(dibenzylamino)ethoxy]benzoyl]-[(3-phenoxyphenyl)methyl]amino]propanoate Chemical compound C=1C=C(OCCN(CC=2C=CC=CC=2)CC=2C=CC=CC=2)C=CC=1C(=O)N(CCC(=O)OC)CC(C=1)=CC=CC=1OC1=CC=CC=C1 UHFWPEQXZWFBKR-UHFFFAOYSA-N 0.000 description 1
- QUXNANIHZLFUDV-UHFFFAOYSA-N methyl 3-[[4-[2-(dibenzylamino)ethoxy]benzoyl]-[(4-phenoxyphenyl)methyl]amino]propanoate Chemical compound C=1C=C(OCCN(CC=2C=CC=CC=2)CC=2C=CC=CC=2)C=CC=1C(=O)N(CCC(=O)OC)CC(C=C1)=CC=C1OC1=CC=CC=C1 QUXNANIHZLFUDV-UHFFFAOYSA-N 0.000 description 1
- MXJRZJXTXRIZNF-UHFFFAOYSA-N methyl 4-(2-naphthalen-2-ylethoxy)benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1OCCC1=CC=C(C=CC=C2)C2=C1 MXJRZJXTXRIZNF-UHFFFAOYSA-N 0.000 description 1
- CSXDNRFMZCQVTK-UHFFFAOYSA-N methyl 4-(2-pyridin-2-ylethoxy)benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1OCCC1=CC=CC=N1 CSXDNRFMZCQVTK-UHFFFAOYSA-N 0.000 description 1
- RRIKCTPGZLYVPC-UHFFFAOYSA-N methyl 4-[2-(3-methylquinoxalin-2-yl)oxyethoxy]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1OCCOC1=NC2=CC=CC=C2N=C1C RRIKCTPGZLYVPC-UHFFFAOYSA-N 0.000 description 1
- OYPSEIIEAMKTGH-UHFFFAOYSA-N methyl 4-[2-(benzylamino)ethoxy]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1OCCNCC1=CC=CC=C1 OYPSEIIEAMKTGH-UHFFFAOYSA-N 0.000 description 1
- CFFMFHSZSKQCRD-UHFFFAOYSA-N methyl 4-[2-(dibenzylamino)ethoxy]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1OCCN(CC=1C=CC=CC=1)CC1=CC=CC=C1 CFFMFHSZSKQCRD-UHFFFAOYSA-N 0.000 description 1
- SLWSWGOEZMOYIG-UHFFFAOYSA-N methyl 4-[2-[benzyl-(2,2,2-trifluoroacetyl)amino]ethoxy]benzoate Chemical compound COC(=O)c1ccc(OCCN(Cc2ccccc2)C(=O)C(F)(F)F)cc1 SLWSWGOEZMOYIG-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
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- 239000002547 new drug Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 108020004017 nuclear receptors Proteins 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
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- 150000002989 phenols Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- 229960005095 pioglitazone Drugs 0.000 description 1
- 238000003752 polymerase chain reaction Methods 0.000 description 1
- 230000023603 positive regulation of transcription initiation, DNA-dependent Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000002287 radioligand Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000005932 reductive alkylation reaction Methods 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 150000004492 retinoid derivatives Chemical class 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 229960004586 rosiglitazone Drugs 0.000 description 1
- 238000001542 size-exclusion chromatography Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000000527 sonication Methods 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
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- 150000003457 sulfones Chemical class 0.000 description 1
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- 239000005495 thyroid hormone Substances 0.000 description 1
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Classifications
-
- 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
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- C07C235/52—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by carboxyl groups
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- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
- C07D215/20—Oxygen atoms
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- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
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- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
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- C07D241/44—Benzopyrazines 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 carbon atoms of the hetero ring
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- C07D277/62—Benzothiazoles
- C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
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- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/16—Radicals substituted by singly bound hetero atoms other than halogen by oxygen atoms
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Quinoline Compounds (AREA)
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- Pyridine Compounds (AREA)
- Indole Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
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| PCT/EP2004/006330 WO2004110983A2 (en) | 2003-06-13 | 2004-06-11 | New benzamides as pparϒ modulators |
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| AU2003265398A1 (en) | 2002-08-09 | 2004-02-25 | Transtech Pharma, Inc. | Aryl and heteroaryl compounds and methods to modulate coagulation |
| US7501538B2 (en) | 2003-08-08 | 2009-03-10 | Transtech Pharma, Inc. | Aryl and heteroaryl compounds, compositions and methods of use |
| US7208601B2 (en) | 2003-08-08 | 2007-04-24 | Mjalli Adnan M M | Aryl and heteroaryl compounds, compositions, and methods of use |
| DE102005004885B4 (de) * | 2005-02-03 | 2010-09-30 | Bruker Daltonik Gmbh | Transport von Ionen ins Vakuum |
| JP5311822B2 (ja) | 2005-07-19 | 2013-10-09 | 第一三共株式会社 | 置換プロパンアミド誘導体及びそれを含む医薬組成物 |
| EP1911744B1 (en) * | 2005-07-20 | 2013-09-04 | Masanori Somei | Tryptophan derivative and use thereof |
| WO2008094860A2 (en) | 2007-01-30 | 2008-08-07 | Allergan, Inc. | Treating ocular diseases using peroxisome proliferator-activated receptor delta antagonists |
| AU2008338963A1 (en) * | 2007-12-13 | 2009-06-25 | Sri International | PPAR-delta ligands and methods of their use |
| US8372885B2 (en) * | 2008-09-17 | 2013-02-12 | Novartis Ag | Organic compounds and their uses |
| CN103201279A (zh) * | 2010-11-05 | 2013-07-10 | 赛诺米克斯公司 | 作为trpm8的调节剂有用的化合物 |
| JP6007417B2 (ja) | 2011-05-31 | 2016-10-12 | レセプトス エルエルシー | 新規glp−1受容体安定剤および調節剤 |
| CN109867630A (zh) | 2013-06-11 | 2019-06-11 | 赛尔基因第二国际有限公司 | 新型glp-1受体调节剂 |
| ES2844573T3 (es) | 2014-12-10 | 2021-07-22 | Receptos Llc | Moduladores del receptor de GLP-1 |
| CN108473484B (zh) | 2015-10-01 | 2021-06-29 | 弗门尼舍公司 | 可用作trpm8调节剂的化合物 |
| CN107176914B (zh) * | 2016-03-09 | 2022-06-28 | 浙江旭晨医药科技有限公司 | 新型gvs系列化合物及其用途 |
| WO2018011230A1 (en) * | 2016-07-13 | 2018-01-18 | Universite D'aix-Marseille | Peroxisome proliferator-activated receptor gamma agonists, method of preparation and uses thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997027847A1 (en) * | 1996-02-02 | 1997-08-07 | Merck & Co., Inc. | Method of treating diabetes and related disease states |
| WO2000055118A1 (en) * | 1999-03-16 | 2000-09-21 | Glaxo Group Limited | Nuclear receptor arylating compounds |
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| EP0849256B1 (en) * | 1995-08-22 | 2005-06-08 | Japan Tobacco Inc. | Amide compounds and use of the same |
| JPH09124571A (ja) * | 1995-11-01 | 1997-05-13 | Japan Tobacco Inc | アミド化合物及びその用途 |
| TWI302149B (en) * | 1999-09-22 | 2008-10-21 | Bristol Myers Squibb Co | Substituted acid derivatives useful as antiodiabetic and antiobesity agents and method |
| AU2003265398A1 (en) * | 2002-08-09 | 2004-02-25 | Transtech Pharma, Inc. | Aryl and heteroaryl compounds and methods to modulate coagulation |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997027847A1 (en) * | 1996-02-02 | 1997-08-07 | Merck & Co., Inc. | Method of treating diabetes and related disease states |
| WO2000055118A1 (en) * | 1999-03-16 | 2000-09-21 | Glaxo Group Limited | Nuclear receptor arylating compounds |
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| AU2004247389A1 (en) | 2004-12-23 |
| EA200600023A1 (ru) | 2006-08-25 |
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| US20060160894A1 (en) | 2006-07-20 |
| WO2004110983A8 (en) | 2005-05-26 |
| ECSP056260A (es) | 2006-04-19 |
| AU2004247389B2 (en) | 2009-12-10 |
| DE602004031339D1 (de) | 2011-03-24 |
| NZ544468A (en) | 2009-09-25 |
| UA84429C2 (ru) | 2008-10-27 |
| GEP20084477B (en) | 2008-09-10 |
| WO2004110983A2 (en) | 2004-12-23 |
| KR20060061300A (ko) | 2006-06-07 |
| EP1644321A2 (en) | 2006-04-12 |
| WO2004110983A3 (en) | 2005-02-10 |
| CN1835914A (zh) | 2006-09-20 |
| EP1644321B1 (en) | 2011-02-09 |
| CR8173A (es) | 2006-05-31 |
| JP2006527233A (ja) | 2006-11-30 |
| CA2528231A1 (en) | 2004-12-23 |
| BRPI0411412A (pt) | 2006-07-25 |
| AU2004247389C1 (en) | 2010-05-27 |
| MXPA05013653A (es) | 2006-02-24 |
| IL172385A0 (en) | 2006-04-10 |
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