TW200528438A - 4-((phenoxyalkyl)thio)-phenoxyacetic acids and analogs - Google Patents

Info

Publication number

TW200528438A

TW200528438A TW093132849A TW93132849A TW200528438A TW 200528438 A TW200528438 A TW 200528438A TW 093132849 A TW093132849 A TW 093132849A TW 93132849 A TW93132849 A TW 93132849A TW 200528438 A TW200528438 A TW 200528438A

Authority

TW

Taiwan

Prior art keywords

fluorenyl

methyl

phenyl

propionic acid

thiadiazol

Prior art date

2003-10-31

Links

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• 125000005359 phenoxyalkyl group Chemical group 0.000 title abstract description 3
• 239000000203 mixture Substances 0.000 claims abstract description 76
• 238000000034 method Methods 0.000 claims abstract description 60
• -1 lactyl Chemical group 0.000 claims description 271
• 150000001875 compounds Chemical class 0.000 claims description 173
• 125000000217 alkyl group Chemical group 0.000 claims description 60
• XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 56
• 230000000694 effects Effects 0.000 claims description 44
• 239000002253 acid Substances 0.000 claims description 40
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 29
• 238000011282 treatment Methods 0.000 claims description 29
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 28
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 28
• 125000003545 alkoxy group Chemical group 0.000 claims description 23
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
• UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 22
• 201000010099 disease Diseases 0.000 claims description 22
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 22
• 239000003814 drug Substances 0.000 claims description 20
• 150000003839 salts Chemical class 0.000 claims description 17
• 206010012601 diabetes mellitus Diseases 0.000 claims description 16
• 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 16
• 229940079593 drug Drugs 0.000 claims description 15
• 125000005843 halogen group Chemical group 0.000 claims description 15
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 14
• 239000000460 chlorine Substances 0.000 claims description 13
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 13
• WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 12
• 229910052757 nitrogen Inorganic materials 0.000 claims description 12
• IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 12
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 11
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 11
• 239000011737 fluorine Substances 0.000 claims description 11
• 229910052731 fluorine Inorganic materials 0.000 claims description 11
• KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 claims description 11
• 229910052801 chlorine Inorganic materials 0.000 claims description 10
• 239000008103 glucose Substances 0.000 claims description 10
• 125000005842 heteroatom Chemical group 0.000 claims description 10
• 208000024891 symptom Diseases 0.000 claims description 10
• VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims description 10
• OBAXVFVUSUVXMM-UHFFFAOYSA-N C12=CC=CC=C2CC2=C1C=CC=C2C(C(O)=O)C Chemical compound C12=CC=CC=C2CC2=C1C=CC=C2C(C(O)=O)C OBAXVFVUSUVXMM-UHFFFAOYSA-N 0.000 claims description 9
• 208000031226 Hyperlipidaemia Diseases 0.000 claims description 9
• 206010022489 Insulin Resistance Diseases 0.000 claims description 9
• 238000011161 development Methods 0.000 claims description 9
• 229910052739 hydrogen Inorganic materials 0.000 claims description 9
• RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 claims description 8
• NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 8
• 125000003003 spiro group Chemical group 0.000 claims description 8
• 238000006243 chemical reaction Methods 0.000 claims description 7
• 238000010586 diagram Methods 0.000 claims description 7
• 125000000623 heterocyclic group Chemical group 0.000 claims description 7
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
• 239000008194 pharmaceutical composition Substances 0.000 claims description 7
• 235000019260 propionic acid Nutrition 0.000 claims description 7
• 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 claims description 6
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• 239000003937 drug carrier Substances 0.000 claims description 6
• 125000003396 thiol group Chemical group [H]S* 0.000 claims description 6
• UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims description 6
• 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 5
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• 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
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• 150000003254 radicals Chemical class 0.000 claims description 5
• 208000011580 syndromic disease Diseases 0.000 claims description 5
• 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 4
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• 239000008267 milk Substances 0.000 claims description 4
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• 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 4
• 239000000126 substance Substances 0.000 claims description 4
• 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 4
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 3
• 230000001771 impaired effect Effects 0.000 claims description 3
• 208000034189 Sclerosis Diseases 0.000 claims description 2
• 150000001335 aliphatic alkanes Chemical class 0.000 claims description 2
• 210000004369 blood Anatomy 0.000 claims description 2
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• 125000000068 chlorophenyl group Chemical group 0.000 claims description 2
• 125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 claims description 2
• GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 2
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• OIWIYLWZIIJNHU-UHFFFAOYSA-N 1-sulfanylpyrazole Chemical compound SN1C=CC=N1 OIWIYLWZIIJNHU-UHFFFAOYSA-N 0.000 claims 2
• 125000003652 trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims 2
• 102100038831 Peroxisome proliferator-activated receptor alpha Human genes 0.000 claims 1
• 102100038825 Peroxisome proliferator-activated receptor gamma Human genes 0.000 claims 1
• 125000002704 decyl 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])C([H])([H])C([H])([H])* 0.000 claims 1
• 230000002452 interceptive effect Effects 0.000 claims 1
• 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
• 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 1
• 208000032928 Dyslipidaemia Diseases 0.000 abstract description 9
• 208000017170 Lipid metabolism disease Diseases 0.000 abstract description 9
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• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 116
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• 238000005481 NMR spectroscopy Methods 0.000 description 107
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• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 65
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