NO327132B1 - Dihydronaftalenderivat-forbindelser og legemidler innholdende disse forbindelsene som den aktive bestanddel - Google Patents
Dihydronaftalenderivat-forbindelser og legemidler innholdende disse forbindelsene som den aktive bestanddel Download PDFInfo
- Publication number
- NO327132B1 NO327132B1 NO20032895A NO20032895A NO327132B1 NO 327132 B1 NO327132 B1 NO 327132B1 NO 20032895 A NO20032895 A NO 20032895A NO 20032895 A NO20032895 A NO 20032895A NO 327132 B1 NO327132 B1 NO 327132B1
- Authority
- NO
- Norway
- Prior art keywords
- ethoxy
- methyloxazol
- dihydronaphthalen
- propanoic acid
- methylthiazol
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 241
- 239000004480 active ingredient Substances 0.000 title claims abstract description 17
- -1 Dihydronaphthalene derivative compounds Chemical class 0.000 title claims description 74
- 239000003814 drug Substances 0.000 title abstract 2
- 229940079593 drug Drugs 0.000 title abstract 2
- 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 claims abstract description 76
- 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 claims abstract description 76
- 150000003839 salts Chemical class 0.000 claims abstract description 48
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 33
- 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 19
- 208000031226 Hyperlipidaemia Diseases 0.000 claims abstract description 18
- 229940126904 hypoglycaemic agent Drugs 0.000 claims abstract description 14
- 208000011580 syndromic disease Diseases 0.000 claims abstract description 14
- 201000001320 Atherosclerosis Diseases 0.000 claims abstract description 13
- 239000003472 antidiabetic agent Substances 0.000 claims abstract description 13
- 201000010099 disease Diseases 0.000 claims abstract description 13
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 13
- 206010020772 Hypertension Diseases 0.000 claims abstract description 10
- 239000003524 antilipemic agent Substances 0.000 claims abstract description 10
- 208000008589 Obesity Diseases 0.000 claims abstract description 8
- 235000020824 obesity Nutrition 0.000 claims abstract description 8
- 208000029078 coronary artery disease Diseases 0.000 claims abstract description 7
- 208000030159 metabolic disease Diseases 0.000 claims abstract description 7
- 208000035150 Hypercholesterolemia Diseases 0.000 claims abstract description 6
- 208000020346 hyperlipoproteinemia Diseases 0.000 claims abstract description 6
- 230000003449 preventive effect Effects 0.000 claims abstract description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 467
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 60
- 231100000252 nontoxic Toxicity 0.000 claims description 37
- 230000003000 nontoxic effect Effects 0.000 claims description 37
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 32
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 30
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 125000002947 alkylene group Chemical group 0.000 claims description 22
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 18
- 239000000556 agonist Substances 0.000 claims description 16
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 claims description 15
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 10
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 235000019260 propionic acid Nutrition 0.000 claims description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 9
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 8
- HNBDRPTVWVGKBR-UHFFFAOYSA-N methyl pentanoate Chemical compound CCCCC(=O)OC HNBDRPTVWVGKBR-UHFFFAOYSA-N 0.000 claims description 8
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 7
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims description 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 4
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 3
- YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical compound C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 claims description 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 description 2
- YKSWONDEPNCRJE-UHFFFAOYSA-N 2,2-dimethyl-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(CC(C)(C)C(O)=O)C=3C=CC=2)=C(C)OC=1C1=CC=CC=C1 YKSWONDEPNCRJE-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- DAYDWNRWCQAKSN-UHFFFAOYSA-N 3-[5-[2-[2-(2,2-difluoro-1,3-benzodioxol-5-yl)-5-methyl-1,3-oxazol-4-yl]ethoxy]-3,4-dihydronaphthalen-1-yl]propanoic acid Chemical compound C1=C2OC(F)(F)OC2=CC(C=2OC(=C(N=2)CCOC=2C=3CCC=C(CCC(O)=O)C=3C=CC=2)C)=C1 DAYDWNRWCQAKSN-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 2
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- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 239000003529 anticholesteremic agent Substances 0.000 claims description 2
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- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
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- GZXURABUWKBDLD-UHFFFAOYSA-N methyl 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]propanoate Chemical compound C1=CC=C2C(CC(C)(C)C(=O)OC)=CCCC2=C1OCCC(=C(O1)C)N=C1C(C=N1)=CC=C1N1CCOCC1 GZXURABUWKBDLD-UHFFFAOYSA-N 0.000 claims description 2
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- 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 description 2
- OVXNABDDUSAJHW-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]-2,2-dimethylpropanoate Chemical compound C1=CC=C2C(CC(C)(C)C(=O)OC)=CCCC2=C1OCCC(=C(O1)C)N=C1C1=CC=C(N(C)C)N=C1 OVXNABDDUSAJHW-UHFFFAOYSA-N 0.000 claims description 2
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- 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 description 2
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- 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
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- 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
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- HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 1
- 239000000391 magnesium silicate Substances 0.000 description 1
- 229910052919 magnesium silicate Inorganic materials 0.000 description 1
- 235000019792 magnesium silicate Nutrition 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 239000003550 marker Substances 0.000 description 1
- 108020004999 messenger RNA Proteins 0.000 description 1
- 125000005905 mesyloxy group Chemical group 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- FQPFECCIWLWKER-UHFFFAOYSA-N methyl 2-[5-methyl-2-(4-methylphenyl)-1,3-oxazol-4-yl]acetate Chemical compound O1C(C)=C(CC(=O)OC)N=C1C1=CC=C(C)C=C1 FQPFECCIWLWKER-UHFFFAOYSA-N 0.000 description 1
- ZMTUNDDCBANJTF-UHFFFAOYSA-N methyl 3-(5-hydroxy-3,4-dihydronaphthalen-1-yl)-2,2-dimethylpropanoate Chemical compound C1=CC=C2C(CC(C)(C)C(=O)OC)=CCCC2=C1O ZMTUNDDCBANJTF-UHFFFAOYSA-N 0.000 description 1
- HDLKFUAFZKXSNJ-UHFFFAOYSA-N methyl 3-(5-hydroxy-3,4-dihydronaphthalen-1-yl)-2-phenylmethoxypropanoate Chemical compound C=1CCC2=C(O)C=CC=C2C=1CC(C(=O)OC)OCC1=CC=CC=C1 HDLKFUAFZKXSNJ-UHFFFAOYSA-N 0.000 description 1
- WHHZMNSFURKYQI-UHFFFAOYSA-N methyl 3-(5-hydroxy-3,4-dihydronaphthalen-1-yl)propanoate Chemical compound C1=CC=C2C(CCC(=O)OC)=CCCC2=C1O WHHZMNSFURKYQI-UHFFFAOYSA-N 0.000 description 1
- RZINTODIHGEBKN-UHFFFAOYSA-N methyl 3-[(4-methylbenzoyl)amino]-4-oxopentanoate Chemical compound COC(=O)CC(C(C)=O)NC(=O)C1=CC=C(C)C=C1 RZINTODIHGEBKN-UHFFFAOYSA-N 0.000 description 1
- CLMKWHOXPFSCME-UHFFFAOYSA-N methyl 3-[5-(methoxymethoxy)-3,4-dihydronaphthalen-1-yl]-2,2-dimethylpropanoate Chemical compound COC(=O)C(C)(C)CC1=CCCC2=C1C=CC=C2OCOC CLMKWHOXPFSCME-UHFFFAOYSA-N 0.000 description 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 description 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 description 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 description 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 description 1
- NXOPIPPPWZTJHJ-UHFFFAOYSA-N methyl 5-(5-hydroxy-3,4-dihydronaphthalen-1-yl)-2,2-dimethylpentanoate Chemical compound C1=CC=C2C(CCCC(C)(C)C(=O)OC)=CCCC2=C1O NXOPIPPPWZTJHJ-UHFFFAOYSA-N 0.000 description 1
- YGMVXTMRAUNZCY-UHFFFAOYSA-N methyl 5-(5-hydroxy-3,4-dihydronaphthalen-1-yl)pentanoate Chemical compound C1=CC=C2C(CCCCC(=O)OC)=CCCC2=C1O YGMVXTMRAUNZCY-UHFFFAOYSA-N 0.000 description 1
- SJXKBJHSHWKTDS-UHFFFAOYSA-N methyl 5-(5-methoxy-3,4-dihydro-2h-naphthalen-1-ylidene)pentanoate Chemical compound C1=CC=C2C(=CCCCC(=O)OC)CCCC2=C1OC SJXKBJHSHWKTDS-UHFFFAOYSA-N 0.000 description 1
- JSRJITATIIVFFE-UHFFFAOYSA-N methyl 5-(5-methoxy-3,4-dihydronaphthalen-1-yl)-2,2-dimethylpentanoate Chemical compound C1=CC=C2C(CCCC(C)(C)C(=O)OC)=CCCC2=C1OC JSRJITATIIVFFE-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- VQNRCYRHRSXAFM-UHFFFAOYSA-N n-(2-methoxypropan-2-yloxy)-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(CCC(=O)NOC(C)(C)OC)=CCCC2=C1OCCC(=C(O1)C)N=C1C1=CC=C(C)C=C1 VQNRCYRHRSXAFM-UHFFFAOYSA-N 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 230000005937 nuclear translocation Effects 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- HAWYTJZHQIXQCP-UHFFFAOYSA-N o-(2-methoxypropan-2-yl)hydroxylamine Chemical compound COC(C)(C)ON HAWYTJZHQIXQCP-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005447 octyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 238000010397 one-hybrid screening Methods 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 229940056360 penicillin g Drugs 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 229940021222 peritoneal dialysis isotonic solution Drugs 0.000 description 1
- 239000002508 peroxisome proliferator activated receptor antagonist Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 229940068968 polysorbate 80 Drugs 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 230000000291 postprandial effect Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 1
- 108060006633 protein kinase Proteins 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 210000001525 retina Anatomy 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 210000000813 small intestine Anatomy 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- ADZXDZREUDDBDZ-UHFFFAOYSA-M sodium;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]propanoate Chemical compound [Na+].N=1C(CCOC=2C=3CCC=C(CC(C)(C)C([O-])=O)C=3C=CC=2)=C(C)OC=1C(C=N1)=CC=C1N1CCOCC1 ADZXDZREUDDBDZ-UHFFFAOYSA-M 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 210000000952 spleen Anatomy 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 229960002385 streptomycin sulfate Drugs 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000008400 supply water Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 238000013519 translation Methods 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- SEDZOYHHAIAQIW-UHFFFAOYSA-N trimethylsilyl azide Chemical compound C[Si](C)(C)N=[N+]=[N-] SEDZOYHHAIAQIW-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- GXPHKUHSUJUWKP-UHFFFAOYSA-N troglitazone Chemical compound C1CC=2C(C)=C(O)C(C)=C(C)C=2OC1(C)COC(C=C1)=CC=C1CC1SC(=O)NC1=O GXPHKUHSUJUWKP-UHFFFAOYSA-N 0.000 description 1
- 229960001641 troglitazone Drugs 0.000 description 1
- GXPHKUHSUJUWKP-NTKDMRAZSA-N troglitazone Natural products C([C@@]1(OC=2C(C)=C(C(=C(C)C=2CC1)O)C)C)OC(C=C1)=CC=C1C[C@H]1SC(=O)NC1=O GXPHKUHSUJUWKP-NTKDMRAZSA-N 0.000 description 1
- 239000012588 trypsin Substances 0.000 description 1
- 238000010396 two-hybrid screening Methods 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 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
-
- 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
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- 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
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D277/38—Nitrogen atoms
- C07D277/40—Unsubstituted amino or imino radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D277/38—Nitrogen atoms
- C07D277/42—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- 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
-
- 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
- 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
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2000392723 | 2000-12-25 | ||
PCT/JP2001/011255 WO2002051820A1 (fr) | 2000-12-25 | 2001-12-21 | Composes derives de dihydronaphtalene et medicaments utilisant ces composes comme ingredient actif |
Publications (3)
Publication Number | Publication Date |
---|---|
NO20032895D0 NO20032895D0 (no) | 2003-06-23 |
NO20032895L NO20032895L (no) | 2003-08-25 |
NO327132B1 true NO327132B1 (no) | 2009-04-27 |
Family
ID=18858667
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO20032895A NO327132B1 (no) | 2000-12-25 | 2003-06-23 | Dihydronaftalenderivat-forbindelser og legemidler innholdende disse forbindelsene som den aktive bestanddel |
Country Status (23)
Country | Link |
---|---|
US (2) | US7220864B2 (fr) |
EP (2) | EP1726586A1 (fr) |
JP (1) | JP3491635B2 (fr) |
KR (2) | KR100718906B1 (fr) |
CN (1) | CN100357280C (fr) |
AT (1) | ATE370130T1 (fr) |
BR (1) | BR0116526A (fr) |
CA (1) | CA2432211C (fr) |
CZ (1) | CZ20031772A3 (fr) |
DE (1) | DE60130031T2 (fr) |
DK (1) | DK1354879T3 (fr) |
ES (1) | ES2291378T3 (fr) |
HU (1) | HUP0303636A3 (fr) |
IL (2) | IL156505A0 (fr) |
MX (1) | MXPA03005763A (fr) |
NO (1) | NO327132B1 (fr) |
NZ (1) | NZ526687A (fr) |
PL (1) | PL207798B1 (fr) |
PT (1) | PT1354879E (fr) |
RU (1) | RU2268262C2 (fr) |
TW (1) | TWI235748B (fr) |
WO (1) | WO2002051820A1 (fr) |
ZA (1) | ZA200304913B (fr) |
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 (fr) * | 2002-07-26 | 2004-02-05 | Bayer Pharmaceuticals Corporation | Derives d'acide carboxylique d'indane, de dihydrobenzofurane et de tetrahydronaphthalene et leurs utilisations comme antidiabetiques |
JP2005104951A (ja) * | 2003-01-17 | 2005-04-21 | Kirin Brewery Co Ltd | 血圧降下用組成物および血管柔軟性改善用組成物並びにこれらの機能が付与された食品 |
DE10308351A1 (de) * | 2003-02-27 | 2004-11-25 | Aventis Pharma Deutschland Gmbh | 1,3-substituierte Cycloalkylderivate mit sauren, meist heterocyclischen Gruppen, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
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 |
DE10308354A1 (de) * | 2003-02-27 | 2004-12-23 | Aventis Pharma Deutschland Gmbh | Cycloalkylderivate mit biosteren Carbonsäure-Gruppen, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
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 |
DE10308353A1 (de) * | 2003-02-27 | 2004-12-02 | Aventis Pharma Deutschland Gmbh | Diarylcycloalkylderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
EP1741704A1 (fr) * | 2004-04-20 | 2007-01-10 | Ono Pharmaceutical Co., Ltd. | Procédé d'augmentation de la surface spécifique d'un médicament légèrement soluble |
AU2006311523A1 (en) * | 2005-11-07 | 2007-05-18 | Irm Llc | Oxazole and thiazole PPAR modulator |
JP5718233B2 (ja) | 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 | 甲状腺刺激ホルモン受容体(tshr)の低分子量アゴニスト |
WO2011127388A2 (fr) | 2010-04-08 | 2011-10-13 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Agonistes inverses et antagonistes neutres pour récepteur du tsh |
WO2012027482A2 (fr) * | 2010-08-24 | 2012-03-01 | Georgetown University | Composés, compositions et méthodes associés aux antagonistes des ppar |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE4317320A1 (de) * | 1993-05-25 | 1994-12-01 | Boehringer Mannheim Gmbh | Neue Thiazolidindione und diese enthaltende Arzneimittel |
GB9604242D0 (en) * | 1996-02-28 | 1996-05-01 | Glaxo Wellcome Inc | Chemical compounds |
WO1999011255A1 (fr) * | 1997-08-28 | 1999-03-11 | Ono Pharmaceutical Co., Ltd. | Regulateurs du recepteur active par les agents de proliferation des peroxysomes |
-
2001
- 2001-12-21 CN CNB018226787A patent/CN100357280C/zh not_active Expired - Fee Related
- 2001-12-21 IL IL15650501A patent/IL156505A0/xx unknown
- 2001-12-21 AT AT01994985T patent/ATE370130T1/de active
- 2001-12-21 JP JP2002552915A patent/JP3491635B2/ja not_active Expired - Fee Related
- 2001-12-21 EP EP06119088A patent/EP1726586A1/fr not_active Withdrawn
- 2001-12-21 MX MXPA03005763A patent/MXPA03005763A/es active IP Right Grant
- 2001-12-21 DE DE60130031T patent/DE60130031T2/de not_active Expired - Lifetime
- 2001-12-21 PL PL363583A patent/PL207798B1/pl not_active IP Right Cessation
- 2001-12-21 KR KR1020067012331A patent/KR100718906B1/ko not_active IP Right Cessation
- 2001-12-21 RU RU2003118718/04A patent/RU2268262C2/ru not_active IP Right Cessation
- 2001-12-21 PT PT01994985T patent/PT1354879E/pt unknown
- 2001-12-21 US US10/451,679 patent/US7220864B2/en not_active Expired - Fee Related
- 2001-12-21 ES ES01994985T patent/ES2291378T3/es not_active Expired - Lifetime
- 2001-12-21 NZ NZ526687A patent/NZ526687A/en not_active IP Right Cessation
- 2001-12-21 DK DK01994985T patent/DK1354879T3/da active
- 2001-12-21 CA CA2432211A patent/CA2432211C/fr not_active Expired - Fee Related
- 2001-12-21 WO PCT/JP2001/011255 patent/WO2002051820A1/fr active IP Right Grant
- 2001-12-21 BR BR0116526-7A patent/BR0116526A/pt not_active IP Right Cessation
- 2001-12-21 CZ CZ20031772A patent/CZ20031772A3/cs unknown
- 2001-12-21 HU HU0303636A patent/HUP0303636A3/hu unknown
- 2001-12-21 EP EP01994985A patent/EP1354879B1/fr not_active Expired - Lifetime
- 2001-12-21 KR KR1020037008566A patent/KR100635315B1/ko not_active IP Right Cessation
- 2001-12-24 TW TW090132011A patent/TWI235748B/zh 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/no not_active IP Right Cessation
- 2003-06-24 ZA ZA200304913A patent/ZA200304913B/en unknown
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2006
- 2006-08-17 US US11/505,359 patent/US20060287304A1/en not_active Abandoned
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