RU2003118718A - DIHYDRONAFTALINE DERIVATIVES AND MEDICINAL PRODUCT INCLUDING THE INDICATED DERIVATIVES AS AN ACTIVE INGREDIENT - Google Patents
DIHYDRONAFTALINE DERIVATIVES AND MEDICINAL PRODUCT INCLUDING THE INDICATED DERIVATIVES AS AN ACTIVE INGREDIENTInfo
- Publication number
- RU2003118718A RU2003118718A RU2003118718/04A RU2003118718A RU2003118718A RU 2003118718 A RU2003118718 A RU 2003118718A RU 2003118718/04 A RU2003118718/04 A RU 2003118718/04A RU 2003118718 A RU2003118718 A RU 2003118718A RU 2003118718 A RU2003118718 A RU 2003118718A
- Authority
- RU
- Russia
- Prior art keywords
- ethoxy
- dihydronaphthalen
- methyloxazol
- propanoic acid
- methylthiazol
- Prior art date
Links
- 239000004480 active ingredient Substances 0.000 title claims 7
- KEIFWROAQVVDBN-UHFFFAOYSA-N Dialin Chemical class C1=CC=C2C=CCCC2=C1 KEIFWROAQVVDBN-UHFFFAOYSA-N 0.000 claims 19
- 230000003000 nontoxic Effects 0.000 claims 19
- 231100000252 nontoxic Toxicity 0.000 claims 19
- 150000003839 salts Chemical class 0.000 claims 19
- 239000011780 sodium chloride Substances 0.000 claims 19
- -1 1H-tetrazol-5-yl Chemical group 0.000 claims 14
- XBDQKXXYIPTUBI-UHFFFAOYSA-N propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 11
- 235000019260 propionic acid Nutrition 0.000 claims 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 7
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 5
- 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 claims 4
- 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 claims 4
- 125000003118 aryl group Chemical group 0.000 claims 4
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 3
- 206010012601 Diabetes mellitus Diseases 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 150000004702 methyl esters Chemical class 0.000 claims 2
- 125000004433 nitrogen atoms Chemical group N* 0.000 claims 2
- 125000004430 oxygen atoms Chemical group O* 0.000 claims 2
- 239000003614 peroxisome proliferator Substances 0.000 claims 2
- 125000004434 sulfur atoms Chemical group 0.000 claims 2
- 201000010874 syndrome Diseases 0.000 claims 2
- IOPRMLUJQBVTKG-UHFFFAOYSA-N 2,2-dimethyl-3-[5-[2-(5-methyl-2-morpholin-4-yl-1,3-thiazol-4-yl)ethoxy]-3,4-dihydronaphthalen-1-yl]propanoic acid Chemical compound N=1C(CCOC=2C=3CCC=C(CC(C)(C)C(O)=O)C=3C=CC=2)=C(C)SC=1N1CCOCC1 IOPRMLUJQBVTKG-UHFFFAOYSA-N 0.000 claims 1
- OUYZZWPTXFCKIZ-UHFFFAOYSA-N 2,2-dimethyl-3-[5-[2-(5-methyl-2-piperidin-1-yl-1,3-thiazol-4-yl)ethoxy]-3,4-dihydronaphthalen-1-yl]propanoic acid Chemical compound N=1C(CCOC=2C=3CCC=C(CC(C)(C)C(O)=O)C=3C=CC=2)=C(C)SC=1N1CCCCC1 OUYZZWPTXFCKIZ-UHFFFAOYSA-N 0.000 claims 1
- PYHZPJIVQGQZER-UHFFFAOYSA-N 2,2-dimethyl-3-[5-[2-(5-methyl-2-propan-2-yl-1,3-oxazol-4-yl)ethoxy]-3,4-dihydronaphthalen-1-yl]propanoic acid Chemical compound O1C(C(C)C)=NC(CCOC=2C=3CCC=C(CC(C)(C)C(O)=O)C=3C=CC=2)=C1C PYHZPJIVQGQZER-UHFFFAOYSA-N 0.000 claims 1
- BRFQWALGJXHKCP-UHFFFAOYSA-N 2,2-dimethyl-3-[5-[2-(5-methyl-2-thiomorpholin-4-yl-1,3-thiazol-4-yl)ethoxy]-3,4-dihydronaphthalen-1-yl]propanoic acid Chemical compound N=1C(CCOC=2C=3CCC=C(CC(C)(C)C(O)=O)C=3C=CC=2)=C(C)SC=1N1CCSCC1 BRFQWALGJXHKCP-UHFFFAOYSA-N 0.000 claims 1
- VQUOQRPGORWKHD-UHFFFAOYSA-N 2,2-dimethyl-3-[5-[2-[5-methyl-2-(6-methylpyridin-3-yl)-1,3-oxazol-4-yl]ethoxy]-3,4-dihydronaphthalen-1-yl]propanoic acid Chemical compound N=1C(CCOC=2C=3CCC=C(CC(C)(C)C(O)=O)C=3C=CC=2)=C(C)OC=1C1=CC=C(C)N=C1 VQUOQRPGORWKHD-UHFFFAOYSA-N 0.000 claims 1
- QJQBFMGIBDQUCO-UHFFFAOYSA-N 2,2-dimethyl-3-[5-[2-[5-methyl-2-(6-morpholin-4-ylpyridin-3-yl)-1,3-oxazol-4-yl]ethoxy]-3,4-dihydronaphthalen-1-yl]propanoic acid Chemical compound N=1C(CCOC=2C=3CCC=C(CC(C)(C)C(O)=O)C=3C=CC=2)=C(C)OC=1C(C=N1)=CC=C1N1CCOCC1 QJQBFMGIBDQUCO-UHFFFAOYSA-N 0.000 claims 1
- ZGSFSSJHCPKQCB-UHFFFAOYSA-N 2,2-dimethyl-3-[5-[2-[5-methyl-2-[6-(2H-pyridin-1-yl)pyridin-3-yl]-1,3-oxazol-4-yl]ethoxy]-3,4-dihydronaphthalen-1-yl]propanoic acid Chemical compound N=1C(CCOC=2C=3CCC=C(CC(C)(C)C(O)=O)C=3C=CC=2)=C(C)OC=1C(C=N1)=CC=C1N1CC=CC=C1 ZGSFSSJHCPKQCB-UHFFFAOYSA-N 0.000 claims 1
- SJWJWJZWBTXJAX-UHFFFAOYSA-N 2,2-dimethyl-5-[5-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]-3,4-dihydronaphthalen-1-yl]pentanoic acid Chemical compound N=1C(CCOC=2C=3CCC=C(CCCC(C)(C)C(O)=O)C=3C=CC=2)=C(C)OC=1C1=CC=CC=C1 SJWJWJZWBTXJAX-UHFFFAOYSA-N 0.000 claims 1
- QEZIDEHXGXLSRU-UHFFFAOYSA-N 2-[5-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]-3,4-dihydronaphthalen-1-yl]acetic acid Chemical compound N=1C(CCOC=2C=3CCC=C(CC(O)=O)C=3C=CC=2)=C(C)OC=1C1=CC=CC=C1 QEZIDEHXGXLSRU-UHFFFAOYSA-N 0.000 claims 1
- ZWXQPHICHCAGQB-UHFFFAOYSA-N 2-[5-[2-(5-methyl-2-piperidin-1-yl-1,3-thiazol-4-yl)ethoxy]-3,4-dihydronaphthalen-1-yl]acetaldehyde Chemical compound N=1C(CCOC=2C=3CCC=C(CC=O)C=3C=CC=2)=C(C)SC=1N1CCCCC1 ZWXQPHICHCAGQB-UHFFFAOYSA-N 0.000 claims 1
- RZGGOKVARMIQTE-UHFFFAOYSA-N 2-[5-[2-(5-methyl-2-piperidin-1-yl-1,3-thiazol-4-yl)ethoxy]-3,4-dihydronaphthalen-1-yl]ethanol Chemical compound N=1C(CCOC=2C=3CCC=C(CCO)C=3C=CC=2)=C(C)SC=1N1CCCCC1 RZGGOKVARMIQTE-UHFFFAOYSA-N 0.000 claims 1
- VJVZGIFFEJCZEP-UHFFFAOYSA-N 2-[5-[2-(5-methyl-2-propan-2-yl-1,3-oxazol-4-yl)ethoxy]-3,4-dihydronaphthalen-1-yl]acetaldehyde Chemical compound O1C(C(C)C)=NC(CCOC=2C=3CCC=C(CC=O)C=3C=CC=2)=C1C VJVZGIFFEJCZEP-UHFFFAOYSA-N 0.000 claims 1
- PMEAZZQAIKFCRJ-UHFFFAOYSA-N 2-[5-[2-(5-methyl-2-propan-2-yl-1,3-oxazol-4-yl)ethoxy]-3,4-dihydronaphthalen-1-yl]ethanol Chemical compound O1C(C(C)C)=NC(CCOC=2C=3CCC=C(CCO)C=3C=CC=2)=C1C PMEAZZQAIKFCRJ-UHFFFAOYSA-N 0.000 claims 1
- HZEVDMKILDMDDB-UHFFFAOYSA-N 2-[5-[2-[2-(4-cyclohexylphenyl)-5-methyl-1,3-oxazol-4-yl]ethoxy]-3,4-dihydronaphthalen-1-yl]acetaldehyde Chemical compound N=1C(CCOC=2C=3CCC=C(CC=O)C=3C=CC=2)=C(C)OC=1C(C=C1)=CC=C1C1CCCCC1 HZEVDMKILDMDDB-UHFFFAOYSA-N 0.000 claims 1
- RFPFZLGLDGNDHQ-UHFFFAOYSA-N 2-[5-[2-[2-(4-cyclohexylphenyl)-5-methyl-1,3-oxazol-4-yl]ethoxy]-3,4-dihydronaphthalen-1-yl]ethanol Chemical compound N=1C(CCOC=2C=3CCC=C(CCO)C=3C=CC=2)=C(C)OC=1C(C=C1)=CC=C1C1CCCCC1 RFPFZLGLDGNDHQ-UHFFFAOYSA-N 0.000 claims 1
- ICSVBMUQHZRRLC-UHFFFAOYSA-N 2-[5-[2-[5-methyl-2-(4-methylphenyl)-1,3-oxazol-4-yl]ethoxy]-3,4-dihydronaphthalen-1-yl]acetaldehyde Chemical compound N=1C(CCOC=2C=3CCC=C(CC=O)C=3C=CC=2)=C(C)OC=1C1=CC=C(C)C=C1 ICSVBMUQHZRRLC-UHFFFAOYSA-N 0.000 claims 1
- MJIAZOUHLLMHLI-UHFFFAOYSA-N 2-[5-[2-[5-methyl-2-(4-methylphenyl)-1,3-oxazol-4-yl]ethoxy]-3,4-dihydronaphthalen-1-yl]acetic acid Chemical compound N=1C(CCOC=2C=3CCC=C(CC(O)=O)C=3C=CC=2)=C(C)OC=1C1=CC=C(C)C=C1 MJIAZOUHLLMHLI-UHFFFAOYSA-N 0.000 claims 1
- MSXDITPOAJXLDQ-UHFFFAOYSA-N 2-[5-[2-[5-methyl-2-(4-methylphenyl)-1,3-oxazol-4-yl]ethoxy]-3,4-dihydronaphthalen-1-yl]ethanol Chemical compound N=1C(CCOC=2C=3CCC=C(CCO)C=3C=CC=2)=C(C)OC=1C1=CC=C(C)C=C1 MSXDITPOAJXLDQ-UHFFFAOYSA-N 0.000 claims 1
- OLPSDQCXNUVQMQ-UHFFFAOYSA-N 2-[5-[2-[5-methyl-2-(4-methylpiperazin-1-yl)-1,3-thiazol-4-yl]ethoxy]-3,4-dihydronaphthalen-1-yl]acetaldehyde Chemical compound C1CN(C)CCN1C1=NC(CCOC=2C=3CCC=C(CC=O)C=3C=CC=2)=C(C)S1 OLPSDQCXNUVQMQ-UHFFFAOYSA-N 0.000 claims 1
- XBKBKSREGXBPCN-UHFFFAOYSA-N 2-[5-[2-[5-methyl-2-(4-methylpiperazin-1-yl)-1,3-thiazol-4-yl]ethoxy]-3,4-dihydronaphthalen-1-yl]ethanol Chemical compound C1CN(C)CCN1C1=NC(CCOC=2C=3CCC=C(CCO)C=3C=CC=2)=C(C)S1 XBKBKSREGXBPCN-UHFFFAOYSA-N 0.000 claims 1
- QJVMSEQITPPVBY-UHFFFAOYSA-N 2-ethoxy-3-[5-[2-(5-methyl-2-piperidin-1-yl-1,3-thiazol-4-yl)ethoxy]-3,4-dihydronaphthalen-1-yl]propanoic acid Chemical compound C1=CC=C2C(CC(OCC)C(O)=O)=CCCC2=C1OCCC(=C(S1)C)N=C1N1CCCCC1 QJVMSEQITPPVBY-UHFFFAOYSA-N 0.000 claims 1
- OWTJXVXAGNGZTA-UHFFFAOYSA-N 2-ethoxy-3-[5-[2-(5-methyl-2-propan-2-yl-1,3-oxazol-4-yl)ethoxy]-3,4-dihydronaphthalen-1-yl]propanoic acid Chemical compound C1=CC=C2C(CC(OCC)C(O)=O)=CCCC2=C1OCCC=1N=C(C(C)C)OC=1C OWTJXVXAGNGZTA-UHFFFAOYSA-N 0.000 claims 1
- XFVAOUUZIRJCHJ-UHFFFAOYSA-N 2-ethoxy-3-[5-[2-[5-methyl-2-(4-methylphenyl)-1,3-oxazol-4-yl]ethoxy]-3,4-dihydronaphthalen-1-yl]propanamide Chemical compound C1=CC=C2C(CC(OCC)C(N)=O)=CCCC2=C1OCCC(=C(O1)C)N=C1C1=CC=C(C)C=C1 XFVAOUUZIRJCHJ-UHFFFAOYSA-N 0.000 claims 1
- YVVXWIQTQFGPNR-UHFFFAOYSA-N 2-ethoxy-3-[5-[2-[5-methyl-2-(4-methylphenyl)-1,3-oxazol-4-yl]ethoxy]-3,4-dihydronaphthalen-1-yl]propanoic acid Chemical compound C1=CC=C2C(CC(OCC)C(O)=O)=CCCC2=C1OCCC(=C(O1)C)N=C1C1=CC=C(C)C=C1 YVVXWIQTQFGPNR-UHFFFAOYSA-N 0.000 claims 1
- WBRNFFXHQHNIBL-UHFFFAOYSA-N 2-ethoxy-3-[5-[2-[5-methyl-2-(4-methylpiperazin-1-yl)-1,3-thiazol-4-yl]ethoxy]-3,4-dihydronaphthalen-1-yl]propanoic acid Chemical compound C1=CC=C2C(CC(OCC)C(O)=O)=CCCC2=C1OCCC(=C(S1)C)N=C1N1CCN(C)CC1 WBRNFFXHQHNIBL-UHFFFAOYSA-N 0.000 claims 1
- WQXCWENYRCQSTP-UHFFFAOYSA-N 3-[5-[2-(5-methyl-2-morpholin-4-yl-1,3-thiazol-4-yl)ethoxy]-3,4-dihydronaphthalen-1-yl]propanoic acid Chemical compound N=1C(CCOC=2C=3CCC=C(CCC(O)=O)C=3C=CC=2)=C(C)SC=1N1CCOCC1 WQXCWENYRCQSTP-UHFFFAOYSA-N 0.000 claims 1
- JJYDONHBIWOQPH-UHFFFAOYSA-N 3-[5-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]-3,4-dihydronaphthalen-1-yl]propanoic acid Chemical compound N=1C(CCOC=2C=3CCC=C(CCC(O)=O)C=3C=CC=2)=C(C)OC=1C1=CC=CC=C1 JJYDONHBIWOQPH-UHFFFAOYSA-N 0.000 claims 1
- FRMUAGFEJSJJHB-UHFFFAOYSA-N 3-[5-[2-(5-methyl-2-piperidin-1-yl-1,3-thiazol-4-yl)ethoxy]-3,4-dihydronaphthalen-1-yl]propanoic acid Chemical compound N=1C(CCOC=2C=3CCC=C(CCC(O)=O)C=3C=CC=2)=C(C)SC=1N1CCCCC1 FRMUAGFEJSJJHB-UHFFFAOYSA-N 0.000 claims 1
- QFVHEXCJXPAPHX-UHFFFAOYSA-N 3-[5-[2-(5-methyl-2-propan-2-yl-1,3-oxazol-4-yl)ethoxy]-3,4-dihydronaphthalen-1-yl]propanoic acid Chemical compound O1C(C(C)C)=NC(CCOC=2C=3CCC=C(CCC(O)=O)C=3C=CC=2)=C1C QFVHEXCJXPAPHX-UHFFFAOYSA-N 0.000 claims 1
- MVOGVQVDJMMFLW-UHFFFAOYSA-N 3-[5-[2-[2-(1,3-benzodioxol-5-yl)-5-methyl-1,3-oxazol-4-yl]ethoxy]-3,4-dihydronaphthalen-1-yl]propanoic acid Chemical compound C1=C2OCOC2=CC(C=2OC(=C(N=2)CCOC=2C=3CCC=C(CCC(O)=O)C=3C=CC=2)C)=C1 MVOGVQVDJMMFLW-UHFFFAOYSA-N 0.000 claims 1
- CQOLDOLSPWVSBZ-UHFFFAOYSA-N 3-[5-[2-[2-(1,5-dimethylpyrazol-3-yl)-5-methyl-1,3-oxazol-4-yl]ethoxy]-3,4-dihydronaphthalen-1-yl]propanoic acid Chemical compound CN1C(C)=CC(C=2OC(C)=C(CCOC=3C=4CCC=C(CCC(O)=O)C=4C=CC=3)N=2)=N1 CQOLDOLSPWVSBZ-UHFFFAOYSA-N 0.000 claims 1
- HIQXLNSZDRGBFP-UHFFFAOYSA-N 3-[5-[2-[2-(3,6-dihydro-2H-pyridin-1-yl)-5-methyl-1,3-thiazol-4-yl]ethoxy]-3,4-dihydronaphthalen-1-yl]propanoic acid Chemical compound N=1C(CCOC=2C=3CCC=C(CCC(O)=O)C=3C=CC=2)=C(C)SC=1N1CCC=CC1 HIQXLNSZDRGBFP-UHFFFAOYSA-N 0.000 claims 1
- MSRZTMZLXIFZGQ-UHFFFAOYSA-N 3-[5-[2-[2-(4-chlorophenyl)-5-methyl-1,3-oxazol-4-yl]ethoxy]-3,4-dihydronaphthalen-1-yl]propanoic acid Chemical compound N=1C(CCOC=2C=3CCC=C(CCC(O)=O)C=3C=CC=2)=C(C)OC=1C1=CC=C(Cl)C=C1 MSRZTMZLXIFZGQ-UHFFFAOYSA-N 0.000 claims 1
- VKUDUELBGZIDIY-UHFFFAOYSA-N 3-[5-[2-[2-(4-cyclohexylphenyl)-5-methyl-1,3-oxazol-4-yl]ethoxy]-3,4-dihydronaphthalen-1-yl]-2-ethoxypropanoic acid Chemical compound C1=CC=C2C(CC(OCC)C(O)=O)=CCCC2=C1OCCC(=C(O1)C)N=C1C(C=C1)=CC=C1C1CCCCC1 VKUDUELBGZIDIY-UHFFFAOYSA-N 0.000 claims 1
- XTHUIUCQHAIWTF-UHFFFAOYSA-N 3-[5-[2-[2-(4-tert-butylphenyl)-5-methyl-1,3-oxazol-4-yl]ethoxy]-3,4-dihydronaphthalen-1-yl]propanoic acid Chemical compound N=1C(CCOC=2C=3CCC=C(CCC(O)=O)C=3C=CC=2)=C(C)OC=1C1=CC=C(C(C)(C)C)C=C1 XTHUIUCQHAIWTF-UHFFFAOYSA-N 0.000 claims 1
- GVSPHPTXGQOKRO-UHFFFAOYSA-N 3-[5-[2-[2-[4-(dimethylamino)phenyl]-5-methyl-1,3-oxazol-4-yl]ethoxy]-3,4-dihydronaphthalen-1-yl]propanoic acid Chemical compound C1=CC(N(C)C)=CC=C1C1=NC(CCOC=2C=3CCC=C(CCC(O)=O)C=3C=CC=2)=C(C)O1 GVSPHPTXGQOKRO-UHFFFAOYSA-N 0.000 claims 1
- IYHIXAFUOZJLIJ-UHFFFAOYSA-N 3-[5-[2-[2-[6-(diethylamino)pyridin-3-yl]-5-methyl-1,3-oxazol-4-yl]ethoxy]-3,4-dihydronaphthalen-1-yl]propanoic acid Chemical compound C1=NC(N(CC)CC)=CC=C1C1=NC(CCOC=2C=3CCC=C(CCC(O)=O)C=3C=CC=2)=C(C)O1 IYHIXAFUOZJLIJ-UHFFFAOYSA-N 0.000 claims 1
- OSWODWPKQYRWJF-UHFFFAOYSA-N 3-[5-[2-[2-[6-(dimethylamino)pyridin-3-yl]-5-methyl-1,3-oxazol-4-yl]ethoxy]-3,4-dihydronaphthalen-1-yl]-2,2-dimethylpropanoic acid Chemical compound C1=NC(N(C)C)=CC=C1C1=NC(CCOC=2C=3CCC=C(CC(C)(C)C(O)=O)C=3C=CC=2)=C(C)O1 OSWODWPKQYRWJF-UHFFFAOYSA-N 0.000 claims 1
- YDOWEZMSMMIPNW-UHFFFAOYSA-N 3-[5-[2-[2-[6-(dimethylamino)pyridin-3-yl]-5-methyl-1,3-oxazol-4-yl]ethoxy]-3,4-dihydronaphthalen-1-yl]propanoic acid Chemical compound C1=NC(N(C)C)=CC=C1C1=NC(CCOC=2C=3CCC=C(CCC(O)=O)C=3C=CC=2)=C(C)O1 YDOWEZMSMMIPNW-UHFFFAOYSA-N 0.000 claims 1
- LCSHACFHRKXOII-UHFFFAOYSA-N 3-[5-[2-[5-methyl-2-(4-methylphenyl)-1,3-oxazol-4-yl]ethoxy]-3,4-dihydronaphthalen-1-yl]-2-phenylmethoxypropanoic acid Chemical compound CC=1OC(C=2C=CC(C)=CC=2)=NC=1CCOC(C=1CCC=2)=CC=CC=1C=2CC(C(O)=O)OCC1=CC=CC=C1 LCSHACFHRKXOII-UHFFFAOYSA-N 0.000 claims 1
- JDLDEQILROFGQI-UHFFFAOYSA-N 3-[5-[2-[5-methyl-2-(4-methylphenyl)-1,3-oxazol-4-yl]ethoxy]-3,4-dihydronaphthalen-1-yl]propan-1-ol Chemical compound N=1C(CCOC=2C=3CCC=C(CCCO)C=3C=CC=2)=C(C)OC=1C1=CC=C(C)C=C1 JDLDEQILROFGQI-UHFFFAOYSA-N 0.000 claims 1
- FVVRFUWPRLNMJM-UHFFFAOYSA-N 3-[5-[2-[5-methyl-2-(4-methylphenyl)-1,3-oxazol-4-yl]ethoxy]-3,4-dihydronaphthalen-1-yl]propanamide Chemical compound N=1C(CCOC=2C=3CCC=C(CCC(N)=O)C=3C=CC=2)=C(C)OC=1C1=CC=C(C)C=C1 FVVRFUWPRLNMJM-UHFFFAOYSA-N 0.000 claims 1
- FBCZFPSQICQIDM-UHFFFAOYSA-N 3-[5-[2-[5-methyl-2-(4-methylphenyl)-1,3-oxazol-4-yl]ethoxy]-3,4-dihydronaphthalen-1-yl]propanoic acid Chemical compound N=1C(CCOC=2C=3CCC=C(CCC(O)=O)C=3C=CC=2)=C(C)OC=1C1=CC=C(C)C=C1 FBCZFPSQICQIDM-UHFFFAOYSA-N 0.000 claims 1
- UKZNEOYTLZSRMX-UHFFFAOYSA-N 3-[5-[2-[5-methyl-2-(4-methylpiperazin-1-yl)-1,3-thiazol-4-yl]ethoxy]-3,4-dihydronaphthalen-1-yl]propanoic acid Chemical compound C1CN(C)CCN1C1=NC(CCOC=2C=3CCC=C(CCC(O)=O)C=3C=CC=2)=C(C)S1 UKZNEOYTLZSRMX-UHFFFAOYSA-N 0.000 claims 1
- ZIKTTZKKJUWJBL-UHFFFAOYSA-N 3-[5-[2-[5-methyl-2-(4-methylpiperidin-1-yl)-1,3-thiazol-4-yl]ethoxy]-3,4-dihydronaphthalen-1-yl]propanoic acid Chemical compound C1CC(C)CCN1C1=NC(CCOC=2C=3CCC=C(CCC(O)=O)C=3C=CC=2)=C(C)S1 ZIKTTZKKJUWJBL-UHFFFAOYSA-N 0.000 claims 1
- ZLXNBBZPNRZDBS-UHFFFAOYSA-N 3-[5-[2-[5-methyl-2-(4-methylsulfanylphenyl)-1,3-oxazol-4-yl]ethoxy]-3,4-dihydronaphthalen-1-yl]propanoic acid Chemical compound C1=CC(SC)=CC=C1C1=NC(CCOC=2C=3CCC=C(CCC(O)=O)C=3C=CC=2)=C(C)O1 ZLXNBBZPNRZDBS-UHFFFAOYSA-N 0.000 claims 1
- KEMTYEUSOQHKRZ-UHFFFAOYSA-N 3-[5-[2-[5-methyl-2-(4-propan-2-ylphenyl)-1,3-oxazol-4-yl]ethoxy]-3,4-dihydronaphthalen-1-yl]propanoic acid Chemical compound C1=CC(C(C)C)=CC=C1C1=NC(CCOC=2C=3CCC=C(CCC(O)=O)C=3C=CC=2)=C(C)O1 KEMTYEUSOQHKRZ-UHFFFAOYSA-N 0.000 claims 1
- QEZYYMOKKQZXEQ-UHFFFAOYSA-N 3-[5-[2-[5-methyl-2-(4-propylphenyl)-1,3-oxazol-4-yl]ethoxy]-3,4-dihydronaphthalen-1-yl]propanoic acid Chemical compound C1=CC(CCC)=CC=C1C1=NC(CCOC=2C=3CCC=C(CCC(O)=O)C=3C=CC=2)=C(C)O1 QEZYYMOKKQZXEQ-UHFFFAOYSA-N 0.000 claims 1
- KJJWAJMFDSXPFP-UHFFFAOYSA-N 3-[5-[2-[5-methyl-2-(5-methylpyrazin-2-yl)-1,3-oxazol-4-yl]ethoxy]-3,4-dihydronaphthalen-1-yl]propanoic acid Chemical compound N=1C(CCOC=2C=3CCC=C(CCC(O)=O)C=3C=CC=2)=C(C)OC=1C1=CN=C(C)C=N1 KJJWAJMFDSXPFP-UHFFFAOYSA-N 0.000 claims 1
- GJAWZWXBSJGGCR-UHFFFAOYSA-N 3-[5-[2-[5-methyl-2-(6-methylpyridin-3-yl)-1,3-oxazol-4-yl]ethoxy]-3,4-dihydronaphthalen-1-yl]propanoic acid Chemical compound N=1C(CCOC=2C=3CCC=C(CCC(O)=O)C=3C=CC=2)=C(C)OC=1C1=CC=C(C)N=C1 GJAWZWXBSJGGCR-UHFFFAOYSA-N 0.000 claims 1
- JTFHSZWBHDVRRO-UHFFFAOYSA-N 3-[5-[2-[5-methyl-2-(6-morpholin-4-ylpyridin-3-yl)-1,3-oxazol-4-yl]ethoxy]-3,4-dihydronaphthalen-1-yl]propanoic acid Chemical compound N=1C(CCOC=2C=3CCC=C(CCC(O)=O)C=3C=CC=2)=C(C)OC=1C(C=N1)=CC=C1N1CCOCC1 JTFHSZWBHDVRRO-UHFFFAOYSA-N 0.000 claims 1
- FPKWDZDICOXWRI-UHFFFAOYSA-N 3-[5-[2-[5-methyl-2-[4-(trifluoromethoxy)phenyl]-1,3-oxazol-4-yl]ethoxy]-3,4-dihydronaphthalen-1-yl]propanoic acid Chemical compound N=1C(CCOC=2C=3CCC=C(CCC(O)=O)C=3C=CC=2)=C(C)OC=1C1=CC=C(OC(F)(F)F)C=C1 FPKWDZDICOXWRI-UHFFFAOYSA-N 0.000 claims 1
- WNRSPFUASAZRMT-UHFFFAOYSA-N 3-[5-[2-[5-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-oxazol-4-yl]ethoxy]-3,4-dihydronaphthalen-1-yl]propanoic acid Chemical compound N=1C(CCOC=2C=3CCC=C(CCC(O)=O)C=3C=CC=2)=C(C)OC=1C1=CC=C(C(F)(F)F)C=C1 WNRSPFUASAZRMT-UHFFFAOYSA-N 0.000 claims 1
- PKHASSDTOIPKBO-UHFFFAOYSA-N 4-[[5-[2-[5-methyl-2-(4-methylphenyl)-1,3-oxazol-4-yl]ethoxy]-3,4-dihydronaphthalen-1-yl]methyl]-1,2-oxazolidine-3,5-dione Chemical compound CC=1OC(C=2C=CC(C)=CC=2)=NC=1CCOC(C=1CCC=2)=CC=CC=1C=2CC1C(=O)NOC1=O PKHASSDTOIPKBO-UHFFFAOYSA-N 0.000 claims 1
- QTLJUSVZEHFIIR-UHFFFAOYSA-N 5-[5-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]-3,4-dihydronaphthalen-1-yl]pentanoic acid Chemical compound N=1C(CCOC=2C=3CCC=C(CCCCC(O)=O)C=3C=CC=2)=C(C)OC=1C1=CC=CC=C1 QTLJUSVZEHFIIR-UHFFFAOYSA-N 0.000 claims 1
- IHBCLWDGFTVRJT-UHFFFAOYSA-N 5-[5-[2-[2-(1,3-benzodioxol-5-yl)-5-methyl-1,3-oxazol-4-yl]ethoxy]-3,4-dihydronaphthalen-1-yl]pentanoic acid Chemical compound C1=C2OCOC2=CC(C=2OC(=C(N=2)CCOC=2C=3CCC=C(CCCCC(O)=O)C=3C=CC=2)C)=C1 IHBCLWDGFTVRJT-UHFFFAOYSA-N 0.000 claims 1
- ZVDAHDWSJNDCDT-UHFFFAOYSA-N 5-[5-[2-[2-[4-(dimethylamino)phenyl]-5-methyl-1,3-oxazol-4-yl]ethoxy]-3,4-dihydronaphthalen-1-yl]pentanoic acid Chemical compound C1=CC(N(C)C)=CC=C1C1=NC(CCOC=2C=3CCC=C(CCCCC(O)=O)C=3C=CC=2)=C(C)O1 ZVDAHDWSJNDCDT-UHFFFAOYSA-N 0.000 claims 1
- ISEOUBQYFAIBBW-UHFFFAOYSA-N 5-[5-[2-[5-methyl-2-(4-methylphenyl)-1,3-oxazol-4-yl]ethoxy]-3,4-dihydronaphthalen-1-yl]pentanoic acid Chemical compound N=1C(CCOC=2C=3CCC=C(CCCCC(O)=O)C=3C=CC=2)=C(C)OC=1C1=CC=C(C)C=C1 ISEOUBQYFAIBBW-UHFFFAOYSA-N 0.000 claims 1
- FIIZZYAGMFUEQW-UHFFFAOYSA-N 5-methyl-2-(4-methylphenyl)-4-[2-[[5-[2-(2H-tetrazol-5-yl)ethyl]-7,8-dihydronaphthalen-1-yl]oxy]ethyl]-1,3-oxazole Chemical compound CC=1OC(C=2C=CC(C)=CC=2)=NC=1CCOC(C=1CCC=2)=CC=CC=1C=2CCC1=NN=NN1 FIIZZYAGMFUEQW-UHFFFAOYSA-N 0.000 claims 1
- 206010003210 Arteriosclerosis Diseases 0.000 claims 1
- YBUMQFBSEMMUDQ-UHFFFAOYSA-N CC(C(=O)O)(C(CC)C1=CCCC2=C(C=CC=C12)OCCC=1N=C(OC=1C)C1=CC=CC=C1)C Chemical compound CC(C(=O)O)(C(CC)C1=CCCC2=C(C=CC=C12)OCCC=1N=C(OC=1C)C1=CC=CC=C1)C YBUMQFBSEMMUDQ-UHFFFAOYSA-N 0.000 claims 1
- 208000004981 Coronary Disease Diseases 0.000 claims 1
- FKRCODPIKNYEAC-UHFFFAOYSA-N Ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 claims 1
- 108010023302 HDL Cholesterol Proteins 0.000 claims 1
- 208000009576 Hypercholesterolemia Diseases 0.000 claims 1
- 206010062060 Hyperlipidaemia Diseases 0.000 claims 1
- 206010020740 Hyperproteinaemia Diseases 0.000 claims 1
- 206010020772 Hypertension Diseases 0.000 claims 1
- 238000008214 LDL Cholesterol Methods 0.000 claims 1
- 108010028554 LDL Cholesterol Proteins 0.000 claims 1
- 208000008466 Metabolic Disease Diseases 0.000 claims 1
- XBBMBQUCFXDJNZ-UHFFFAOYSA-N N1(CCSCC1)C=1SC(=C(N=1)CCOC1=C2CCC=C(C2=CC=C1)C(C(=O)O)C)C Chemical compound N1(CCSCC1)C=1SC(=C(N=1)CCOC1=C2CCC=C(C2=CC=C1)C(C(=O)O)C)C XBBMBQUCFXDJNZ-UHFFFAOYSA-N 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- 108010069201 VLDL Cholesterol Proteins 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- 239000003472 antidiabetic agent Substances 0.000 claims 1
- 239000003524 antilipemic agent Substances 0.000 claims 1
- 201000001320 atherosclerosis Diseases 0.000 claims 1
- RSZVYVRXTAHTNG-UHFFFAOYSA-N ethyl 2-[5-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]-3,4-dihydronaphthalen-1-yl]acetate Chemical compound C1=CC=C2C(CC(=O)OCC)=CCCC2=C1OCCC(=C(O1)C)N=C1C1=CC=CC=C1 RSZVYVRXTAHTNG-UHFFFAOYSA-N 0.000 claims 1
- HOXCYAMZLMWKMI-UHFFFAOYSA-N ethyl 2-[5-[2-(5-methyl-2-piperidin-1-yl-1,3-thiazol-4-yl)ethoxy]-3,4-dihydronaphthalen-1-yl]acetate Chemical compound C1=CC=C2C(CC(=O)OCC)=CCCC2=C1OCCC(=C(S1)C)N=C1N1CCCCC1 HOXCYAMZLMWKMI-UHFFFAOYSA-N 0.000 claims 1
- QFFJHBDHQKPSGM-UHFFFAOYSA-N ethyl 2-[5-[2-(5-methyl-2-propan-2-yl-1,3-oxazol-4-yl)ethoxy]-3,4-dihydronaphthalen-1-yl]acetate Chemical compound C1=CC=C2C(CC(=O)OCC)=CCCC2=C1OCCC=1N=C(C(C)C)OC=1C QFFJHBDHQKPSGM-UHFFFAOYSA-N 0.000 claims 1
- ODIQLWLBPKZXQM-UHFFFAOYSA-N ethyl 2-[5-[2-[2-(4-cyclohexylphenyl)-5-methyl-1,3-oxazol-4-yl]ethoxy]-3,4-dihydronaphthalen-1-yl]acetate Chemical compound C1=CC=C2C(CC(=O)OCC)=CCCC2=C1OCCC(=C(O1)C)N=C1C(C=C1)=CC=C1C1CCCCC1 ODIQLWLBPKZXQM-UHFFFAOYSA-N 0.000 claims 1
- GYCAHFXPAPFGMM-UHFFFAOYSA-N ethyl 2-[5-[2-[5-methyl-2-(4-methylphenyl)-1,3-oxazol-4-yl]ethoxy]-3,4-dihydronaphthalen-1-yl]acetate Chemical compound C1=CC=C2C(CC(=O)OCC)=CCCC2=C1OCCC(=C(O1)C)N=C1C1=CC=C(C)C=C1 GYCAHFXPAPFGMM-UHFFFAOYSA-N 0.000 claims 1
- DSCFWFIIUXJGMZ-UHFFFAOYSA-N ethyl 2-[5-[2-[5-methyl-2-(4-methylpiperazin-1-yl)-1,3-thiazol-4-yl]ethoxy]-3,4-dihydronaphthalen-1-yl]acetate Chemical compound C1=CC=C2C(CC(=O)OCC)=CCCC2=C1OCCC(=C(S1)C)N=C1N1CCN(C)CC1 DSCFWFIIUXJGMZ-UHFFFAOYSA-N 0.000 claims 1
- ZDEFYFWDPKTJOJ-UHFFFAOYSA-N ethyl 3-[5-[2-(5-methyl-2-morpholin-4-yl-1,3-thiazol-4-yl)ethoxy]-3,4-dihydronaphthalen-1-yl]propanoate Chemical compound C1=CC=C2C(CCC(=O)OCC)=CCCC2=C1OCCC(=C(S1)C)N=C1N1CCOCC1 ZDEFYFWDPKTJOJ-UHFFFAOYSA-N 0.000 claims 1
- STFCRJMVPMZODW-UHFFFAOYSA-N ethyl 3-[5-[2-(5-methyl-2-propan-2-yl-1,3-oxazol-4-yl)ethoxy]-3,4-dihydronaphthalen-1-yl]propanoate Chemical compound C1=CC=C2C(CCC(=O)OCC)=CCCC2=C1OCCC=1N=C(C(C)C)OC=1C STFCRJMVPMZODW-UHFFFAOYSA-N 0.000 claims 1
- PNZGJZVOGYEWRS-UHFFFAOYSA-N ethyl 3-[5-[2-(5-methyl-2-thiomorpholin-4-yl-1,3-thiazol-4-yl)ethoxy]-3,4-dihydronaphthalen-1-yl]propanoate Chemical compound C1=CC=C2C(CCC(=O)OCC)=CCCC2=C1OCCC(=C(S1)C)N=C1N1CCSCC1 PNZGJZVOGYEWRS-UHFFFAOYSA-N 0.000 claims 1
- IVOIOFBWFYVFMW-UHFFFAOYSA-N ethyl 3-[5-[2-[2-(1,5-dimethylpyrazol-3-yl)-5-methyl-1,3-oxazol-4-yl]ethoxy]-3,4-dihydronaphthalen-1-yl]propanoate Chemical compound C1=CC=C2C(CCC(=O)OCC)=CCCC2=C1OCCC(=C(O1)C)N=C1C=1C=C(C)N(C)N=1 IVOIOFBWFYVFMW-UHFFFAOYSA-N 0.000 claims 1
- KKHOWXGWBODTNE-UHFFFAOYSA-N ethyl 3-[5-[2-[2-(4-chlorophenyl)-5-methyl-1,3-oxazol-4-yl]ethoxy]-3,4-dihydronaphthalen-1-yl]propanoate Chemical compound C1=CC=C2C(CCC(=O)OCC)=CCCC2=C1OCCC(=C(O1)C)N=C1C1=CC=C(Cl)C=C1 KKHOWXGWBODTNE-UHFFFAOYSA-N 0.000 claims 1
- KVPUWYXBEHHXOL-UHFFFAOYSA-N ethyl 3-[5-[2-[2-[6-(diethylamino)pyridin-3-yl]-5-methyl-1,3-oxazol-4-yl]ethoxy]-3,4-dihydronaphthalen-1-yl]propanoate Chemical compound C1=CC=C2C(CCC(=O)OCC)=CCCC2=C1OCCC(=C(O1)C)N=C1C1=CC=C(N(CC)CC)N=C1 KVPUWYXBEHHXOL-UHFFFAOYSA-N 0.000 claims 1
- DDEQQBLABLZPQP-UHFFFAOYSA-N ethyl 3-[5-[2-[5-methyl-2-(4-methylphenyl)-1,3-oxazol-4-yl]ethoxy]-3,4-dihydronaphthalen-1-yl]propanoate Chemical compound C1=CC=C2C(CCC(=O)OCC)=CCCC2=C1OCCC(=C(O1)C)N=C1C1=CC=C(C)C=C1 DDEQQBLABLZPQP-UHFFFAOYSA-N 0.000 claims 1
- JUABYSLCGQCIGO-UHFFFAOYSA-N ethyl 3-[5-[2-[5-methyl-2-(4-methylpiperazin-1-yl)-1,3-thiazol-4-yl]ethoxy]-3,4-dihydronaphthalen-1-yl]propanoate Chemical compound C1=CC=C2C(CCC(=O)OCC)=CCCC2=C1OCCC(=C(S1)C)N=C1N1CCN(C)CC1 JUABYSLCGQCIGO-UHFFFAOYSA-N 0.000 claims 1
- NONYNFRTHGRHLT-UHFFFAOYSA-N ethyl 3-[5-[2-[5-methyl-2-(4-methylpiperidin-1-yl)-1,3-thiazol-4-yl]ethoxy]-3,4-dihydronaphthalen-1-yl]propanoate Chemical compound C1=CC=C2C(CCC(=O)OCC)=CCCC2=C1OCCC(=C(S1)C)N=C1N1CCC(C)CC1 NONYNFRTHGRHLT-UHFFFAOYSA-N 0.000 claims 1
- YHBYGELOCBNKFN-UHFFFAOYSA-N ethyl 3-[5-[2-[5-methyl-2-(4-methylsulfanylphenyl)-1,3-oxazol-4-yl]ethoxy]-3,4-dihydronaphthalen-1-yl]propanoate Chemical compound C1=CC=C2C(CCC(=O)OCC)=CCCC2=C1OCCC(=C(O1)C)N=C1C1=CC=C(SC)C=C1 YHBYGELOCBNKFN-UHFFFAOYSA-N 0.000 claims 1
- OBPAYRIPWLQAQM-UHFFFAOYSA-N ethyl 3-[5-[2-[5-methyl-2-(4-propan-2-ylphenyl)-1,3-oxazol-4-yl]ethoxy]-3,4-dihydronaphthalen-1-yl]propanoate Chemical compound C1=CC=C2C(CCC(=O)OCC)=CCCC2=C1OCCC(=C(O1)C)N=C1C1=CC=C(C(C)C)C=C1 OBPAYRIPWLQAQM-UHFFFAOYSA-N 0.000 claims 1
- ZFDVCSYBOYSUEB-UHFFFAOYSA-N ethyl 3-[5-[2-[5-methyl-2-(4-propylphenyl)-1,3-oxazol-4-yl]ethoxy]-3,4-dihydronaphthalen-1-yl]propanoate Chemical compound C1=CC(CCC)=CC=C1C1=NC(CCOC=2C=3CCC=C(CCC(=O)OCC)C=3C=CC=2)=C(C)O1 ZFDVCSYBOYSUEB-UHFFFAOYSA-N 0.000 claims 1
- OCFUTOXALKVUKE-UHFFFAOYSA-N ethyl 3-[5-[2-[5-methyl-2-(5-methylpyrazin-2-yl)-1,3-oxazol-4-yl]ethoxy]-3,4-dihydronaphthalen-1-yl]propanoate Chemical compound C1=CC=C2C(CCC(=O)OCC)=CCCC2=C1OCCC(=C(O1)C)N=C1C1=CN=C(C)C=N1 OCFUTOXALKVUKE-UHFFFAOYSA-N 0.000 claims 1
- SLKIBTDXDPQTPS-UHFFFAOYSA-N ethyl 3-[5-[2-[5-methyl-2-(6-methylpyridin-3-yl)-1,3-oxazol-4-yl]ethoxy]-3,4-dihydronaphthalen-1-yl]propanoate Chemical compound C1=CC=C2C(CCC(=O)OCC)=CCCC2=C1OCCC(=C(O1)C)N=C1C1=CC=C(C)N=C1 SLKIBTDXDPQTPS-UHFFFAOYSA-N 0.000 claims 1
- NIPRWSIQZOVDEC-UHFFFAOYSA-N ethyl 3-[5-[2-[5-methyl-2-[4-(trifluoromethoxy)phenyl]-1,3-oxazol-4-yl]ethoxy]-3,4-dihydronaphthalen-1-yl]propanoate Chemical compound C1=CC=C2C(CCC(=O)OCC)=CCCC2=C1OCCC(=C(O1)C)N=C1C1=CC=C(OC(F)(F)F)C=C1 NIPRWSIQZOVDEC-UHFFFAOYSA-N 0.000 claims 1
- OPCZAGLRHMDWOT-UHFFFAOYSA-N ethyl 3-[5-[2-[5-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-oxazol-4-yl]ethoxy]-3,4-dihydronaphthalen-1-yl]propanoate Chemical compound C1=CC=C2C(CCC(=O)OCC)=CCCC2=C1OCCC(=C(O1)C)N=C1C1=CC=C(C(F)(F)F)C=C1 OPCZAGLRHMDWOT-UHFFFAOYSA-N 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 125000005842 heteroatoms Chemical group 0.000 claims 1
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims 1
- BHGGLHPNHNJVHL-UHFFFAOYSA-N methyl 2,2-dimethyl-3-[5-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]-3,4-dihydronaphthalen-1-yl]propanoate Chemical compound C1=CC=C2C(CC(C)(C)C(=O)OC)=CCCC2=C1OCCC(=C(O1)C)N=C1C1=CC=CC=C1 BHGGLHPNHNJVHL-UHFFFAOYSA-N 0.000 claims 1
- JWYXDSYQMLTZCN-UHFFFAOYSA-N methyl 2,2-dimethyl-3-[5-[2-(5-methyl-2-propan-2-yl-1,3-oxazol-4-yl)ethoxy]-3,4-dihydronaphthalen-1-yl]propanoate Chemical compound C1=CC=C2C(CC(C)(C)C(=O)OC)=CCCC2=C1OCCC=1N=C(C(C)C)OC=1C JWYXDSYQMLTZCN-UHFFFAOYSA-N 0.000 claims 1
- YVUSHWZDTBSANQ-UHFFFAOYSA-N methyl 2,2-dimethyl-5-[5-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]-3,4-dihydronaphthalen-1-yl]pentanoate Chemical compound C1=CC=C2C(CCCC(C)(C)C(=O)OC)=CCCC2=C1OCCC(=C(O1)C)N=C1C1=CC=CC=C1 YVUSHWZDTBSANQ-UHFFFAOYSA-N 0.000 claims 1
- KNRHQLAPTGFAJF-UHFFFAOYSA-N methyl 3-[5-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]-3,4-dihydronaphthalen-1-yl]propanoate Chemical compound C1=CC=C2C(CCC(=O)OC)=CCCC2=C1OCCC(=C(O1)C)N=C1C1=CC=CC=C1 KNRHQLAPTGFAJF-UHFFFAOYSA-N 0.000 claims 1
- CJHNCQRHNKFNCH-UHFFFAOYSA-N methyl 3-[5-[2-[2-(1,3-benzodioxol-5-yl)-5-methyl-1,3-oxazol-4-yl]ethoxy]-3,4-dihydronaphthalen-1-yl]propanoate Chemical compound C1=C2OCOC2=CC(C2=NC(=C(O2)C)CCOC2=C3CCC=C(C3=CC=C2)CCC(=O)OC)=C1 CJHNCQRHNKFNCH-UHFFFAOYSA-N 0.000 claims 1
- BPQCLUKBNHOFGK-UHFFFAOYSA-N methyl 3-[5-[2-[2-(4-tert-butylphenyl)-5-methyl-1,3-oxazol-4-yl]ethoxy]-3,4-dihydronaphthalen-1-yl]propanoate Chemical compound C1=CC=C2C(CCC(=O)OC)=CCCC2=C1OCCC(=C(O1)C)N=C1C1=CC=C(C(C)(C)C)C=C1 BPQCLUKBNHOFGK-UHFFFAOYSA-N 0.000 claims 1
- SUFOHUOLEIDTHY-UHFFFAOYSA-N methyl 3-[5-[2-[2-[4-(dimethylamino)phenyl]-5-methyl-1,3-oxazol-4-yl]ethoxy]-3,4-dihydronaphthalen-1-yl]propanoate Chemical compound C1=CC=C2C(CCC(=O)OC)=CCCC2=C1OCCC(=C(O1)C)N=C1C1=CC=C(N(C)C)C=C1 SUFOHUOLEIDTHY-UHFFFAOYSA-N 0.000 claims 1
- CDUHJGGFPDAMAP-UHFFFAOYSA-N methyl 3-[5-[2-[2-[6-(dimethylamino)pyridin-3-yl]-5-methyl-1,3-oxazol-4-yl]ethoxy]-3,4-dihydronaphthalen-1-yl]propanoate Chemical compound C1=CC=C2C(CCC(=O)OC)=CCCC2=C1OCCC(=C(O1)C)N=C1C1=CC=C(N(C)C)N=C1 CDUHJGGFPDAMAP-UHFFFAOYSA-N 0.000 claims 1
- CUKGMFQYORIRJQ-UHFFFAOYSA-N methyl 3-[5-[2-[5-methyl-2-(4-methylphenyl)-1,3-oxazol-4-yl]ethoxy]-3,4-dihydronaphthalen-1-yl]-2-phenylmethoxypropanoate Chemical compound C=1C=CC=CC=1COC(C(=O)OC)CC(C1=CC=C2)=CCCC1=C2OCCC(=C(O1)C)N=C1C1=CC=C(C)C=C1 CUKGMFQYORIRJQ-UHFFFAOYSA-N 0.000 claims 1
- KOTICVJVXZBVLR-UHFFFAOYSA-N methyl 3-[5-[2-[5-methyl-2-(4-methylphenyl)-1,3-oxazol-4-yl]ethoxy]-3,4-dihydronaphthalen-1-yl]propanoate Chemical compound C1=CC=C2C(CCC(=O)OC)=CCCC2=C1OCCC(=C(O1)C)N=C1C1=CC=C(C)C=C1 KOTICVJVXZBVLR-UHFFFAOYSA-N 0.000 claims 1
- BJRXGXNVYRWNIL-UHFFFAOYSA-N methyl 5-[5-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]-3,4-dihydronaphthalen-1-yl]pentanoate Chemical compound C1=CC=C2C(CCCCC(=O)OC)=CCCC2=C1OCCC(=C(O1)C)N=C1C1=CC=CC=C1 BJRXGXNVYRWNIL-UHFFFAOYSA-N 0.000 claims 1
- RMMXPFZSNGWBEY-UHFFFAOYSA-N methyl 5-[5-[2-[2-(1,3-benzodioxol-5-yl)-5-methyl-1,3-oxazol-4-yl]ethoxy]-3,4-dihydronaphthalen-1-yl]pentanoate Chemical compound C1=C2OCOC2=CC(C2=NC(=C(O2)C)CCOC2=C3CCC=C(C3=CC=C2)CCCCC(=O)OC)=C1 RMMXPFZSNGWBEY-UHFFFAOYSA-N 0.000 claims 1
- PQYWYCJQIUQTCN-UHFFFAOYSA-N methyl 5-[5-[2-[2-[4-(dimethylamino)phenyl]-5-methyl-1,3-oxazol-4-yl]ethoxy]-3,4-dihydronaphthalen-1-yl]pentanoate Chemical compound C1=CC=C2C(CCCCC(=O)OC)=CCCC2=C1OCCC(=C(O1)C)N=C1C1=CC=C(N(C)C)C=C1 PQYWYCJQIUQTCN-UHFFFAOYSA-N 0.000 claims 1
- ZKFSVHLMLIXDMC-UHFFFAOYSA-N methyl 5-[5-[2-[5-methyl-2-(4-methylphenyl)-1,3-oxazol-4-yl]ethoxy]-3,4-dihydronaphthalen-1-yl]pentanoate Chemical compound C1=CC=C2C(CCCCC(=O)OC)=CCCC2=C1OCCC(=C(O1)C)N=C1C1=CC=C(C)C=C1 ZKFSVHLMLIXDMC-UHFFFAOYSA-N 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- 235000020830 overeating Nutrition 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 239000000018 receptor agonist Substances 0.000 claims 1
- 108091006057 receptor regulators Proteins 0.000 claims 1
- 102000005962 receptors Human genes 0.000 claims 1
- 108020003175 receptors Proteins 0.000 claims 1
- 239000010802 sludge Substances 0.000 claims 1
Claims (19)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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JP2000-392723 | 2000-12-25 | ||
JP2000392723 | 2000-12-25 |
Publications (2)
Publication Number | Publication Date |
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RU2003118718A true RU2003118718A (en) | 2004-08-20 |
RU2268262C2 RU2268262C2 (en) | 2006-01-20 |
Family
ID=18858667
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
RU2003118718/04A RU2268262C2 (en) | 2000-12-25 | 2001-12-21 | Dihydronaphthalene derivatives and medicinal agent comprising indicated derivatives as active component |
Country Status (23)
Country | Link |
---|---|
US (2) | US7220864B2 (en) |
EP (2) | EP1354879B1 (en) |
JP (1) | JP3491635B2 (en) |
KR (2) | KR100718906B1 (en) |
CN (1) | CN100357280C (en) |
AT (1) | ATE370130T1 (en) |
BR (1) | BR0116526A (en) |
CA (1) | CA2432211C (en) |
CZ (1) | CZ20031772A3 (en) |
DE (1) | DE60130031T2 (en) |
DK (1) | DK1354879T3 (en) |
ES (1) | ES2291378T3 (en) |
HU (1) | HUP0303636A3 (en) |
IL (2) | IL156505A0 (en) |
MX (1) | MXPA03005763A (en) |
NO (1) | NO327132B1 (en) |
NZ (1) | NZ526687A (en) |
PL (1) | PL207798B1 (en) |
PT (1) | PT1354879E (en) |
RU (1) | RU2268262C2 (en) |
TW (1) | TWI235748B (en) |
WO (1) | WO2002051820A1 (en) |
ZA (1) | ZA200304913B (en) |
Families Citing this family (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7375093B2 (en) | 2002-07-05 | 2008-05-20 | Intrexon Corporation | Ketone ligands for modulating the expression of exogenous genes via an ecdysone receptor complex |
WO2004011446A1 (en) * | 2002-07-26 | 2004-02-05 | Bayer Pharmaceuticals Corporation | Indane, dihydrobenzofuran, and tetrahydronaphthalene carboxylic acid derivatives and their use as antidiabetics |
JP2005104951A (en) * | 2003-01-17 | 2005-04-21 | Kirin Brewery Co Ltd | Hypotensive composition, blood vessel flexibility-improving composition, and food imparted with such functions |
DE10308353A1 (en) * | 2003-02-27 | 2004-12-02 | Aventis Pharma Deutschland Gmbh | Diarylcycloalkyl derivatives, processes for their preparation and their use as medicines |
DE10308355A1 (en) * | 2003-02-27 | 2004-12-23 | Aventis Pharma Deutschland Gmbh | Aryl-cycloalkyl-substituted alkanoic acid derivatives, process for their preparation and their use as medicaments |
US7148246B2 (en) | 2003-02-27 | 2006-12-12 | Sanofi-Aventis Deutschland Gmbh | Cycloalkyl derivatives having bioisosteric carboxylic acid groups, processes for their preparation and their use as pharmaceuticals |
DE10308351A1 (en) * | 2003-02-27 | 2004-11-25 | Aventis Pharma Deutschland Gmbh | 1,3-substituted cycloalkyl derivatives having acidic, usually heterocyclic groups, processes for their preparation and their use as medicaments |
DE10308354A1 (en) * | 2003-02-27 | 2004-12-23 | Aventis Pharma Deutschland Gmbh | Cycloalkyl derivatives with biostear carboxylic acid groups, process for their preparation and their use as medicaments |
US20080026067A1 (en) * | 2004-04-20 | 2008-01-31 | Kuwabe Shin-Itsu | Method for Increasing Specific Surface Area of Slightly Soluble Drug |
ES2350600T3 (en) * | 2005-11-07 | 2011-01-25 | Irm Llc | PPAR MODULATOR CONTAINING OXAZOL AND TIAZOL. |
JP5718233B2 (en) | 2008-10-20 | 2015-05-13 | ザ ガバメント オブ ザ ユナイテッド ステイツ オブ アメリカ アズ リプレゼンテッド バイ ザ セクレタリー オブ ザ デパートメント オブ ヘルス アンド ヒューマン サービシーズ | Thyroid-stimulating hormone receptor (TSHR) low molecular weight agonist |
EP2563777A4 (en) | 2010-04-08 | 2013-09-04 | Us Health | Inverse agonists and neutral antagonists for the tsh receptor |
WO2012027482A2 (en) * | 2010-08-24 | 2012-03-01 | Georgetown University | Compounds, compositions and methods related to ppar antagonists |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE4317320A1 (en) * | 1993-05-25 | 1994-12-01 | Boehringer Mannheim Gmbh | New thiazolidinediones and medicines containing them |
GB9604242D0 (en) * | 1996-02-28 | 1996-05-01 | Glaxo Wellcome Inc | Chemical compounds |
WO1999011255A1 (en) * | 1997-08-28 | 1999-03-11 | Ono Pharmaceutical Co., Ltd. | Peroxisome proliferator-activated receptor controllers |
-
2001
- 2001-12-21 AT AT01994985T patent/ATE370130T1/en active
- 2001-12-21 HU HU0303636A patent/HUP0303636A3/en unknown
- 2001-12-21 BR BR0116526-7A patent/BR0116526A/en not_active IP Right Cessation
- 2001-12-21 US US10/451,679 patent/US7220864B2/en not_active Expired - Fee Related
- 2001-12-21 DK DK01994985T patent/DK1354879T3/en active
- 2001-12-21 PT PT01994985T patent/PT1354879E/en unknown
- 2001-12-21 PL PL363583A patent/PL207798B1/en not_active IP Right Cessation
- 2001-12-21 EP EP01994985A patent/EP1354879B1/en not_active Expired - Lifetime
- 2001-12-21 EP EP06119088A patent/EP1726586A1/en not_active Withdrawn
- 2001-12-21 CA CA2432211A patent/CA2432211C/en not_active Expired - Fee Related
- 2001-12-21 JP JP2002552915A patent/JP3491635B2/en not_active Expired - Fee Related
- 2001-12-21 DE DE60130031T patent/DE60130031T2/en not_active Expired - Lifetime
- 2001-12-21 IL IL15650501A patent/IL156505A0/en unknown
- 2001-12-21 WO PCT/JP2001/011255 patent/WO2002051820A1/en active IP Right Grant
- 2001-12-21 MX MXPA03005763A patent/MXPA03005763A/en active IP Right Grant
- 2001-12-21 RU RU2003118718/04A patent/RU2268262C2/en not_active IP Right Cessation
- 2001-12-21 CN CNB018226787A patent/CN100357280C/en not_active Expired - Fee Related
- 2001-12-21 ES ES01994985T patent/ES2291378T3/en not_active Expired - Lifetime
- 2001-12-21 CZ CZ20031772A patent/CZ20031772A3/en unknown
- 2001-12-21 KR KR1020067012331A patent/KR100718906B1/en not_active IP Right Cessation
- 2001-12-21 NZ NZ526687A patent/NZ526687A/en not_active IP Right Cessation
- 2001-12-21 KR KR1020037008566A patent/KR100635315B1/en not_active IP Right Cessation
- 2001-12-24 TW TW090132011A patent/TWI235748B/en not_active IP Right Cessation
-
2003
- 2003-06-18 IL IL156505A patent/IL156505A/en not_active IP Right Cessation
- 2003-06-23 NO NO20032895A patent/NO327132B1/en not_active IP Right Cessation
- 2003-06-24 ZA ZA200304913A patent/ZA200304913B/en unknown
-
2006
- 2006-08-17 US US11/505,359 patent/US20060287304A1/en not_active Abandoned
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