TW200424172A - PPAR activators - Google Patents

Info

Publication number

TW200424172A

TW200424172A TW092133036A TW92133036A TW200424172A TW 200424172 A TW200424172 A TW 200424172A TW 092133036 A TW092133036 A TW 092133036A TW 92133036 A TW92133036 A TW 92133036A TW 200424172 A TW200424172 A TW 200424172A

Authority

TW

Taiwan

Prior art keywords

methyl

acid

group

compound

alkyl

Prior art date

2002-11-26

Links

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• Global Dossier
• Discuss

• 239000012190 activator Substances 0.000 title abstract description 70
• 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 title description 15
• 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 title description 15
• 150000001875 compounds Chemical class 0.000 claims abstract description 593
• 241000124008 Mammalia Species 0.000 claims abstract description 76
• 201000001320 Atherosclerosis Diseases 0.000 claims abstract description 22
• -1 sulfofluorenyl Chemical group 0.000 claims description 224
• 229940002612 prodrug Drugs 0.000 claims description 124
• 239000000651 prodrug Substances 0.000 claims description 124
• 238000000034 method Methods 0.000 claims description 112
• 125000000217 alkyl group Chemical group 0.000 claims description 106
• 239000003112 inhibitor Substances 0.000 claims description 97
• 150000003839 salts Chemical class 0.000 claims description 88
• 238000011282 treatment Methods 0.000 claims description 72
• 239000002253 acid Substances 0.000 claims description 71
• 239000000203 mixture Substances 0.000 claims description 60
• 239000003981 vehicle Substances 0.000 claims description 54
• 229910052757 nitrogen Chemical group 0.000 claims description 53
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 52
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 51
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 48
• 125000003545 alkoxy group Chemical group 0.000 claims description 47
• 239000003814 drug Substances 0.000 claims description 47
• 239000001301 oxygen Substances 0.000 claims description 47
• 229910052760 oxygen Inorganic materials 0.000 claims description 47
• 239000003795 chemical substances by application Substances 0.000 claims description 46
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 45
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 41
• 229910052739 hydrogen Inorganic materials 0.000 claims description 39
• 125000005843 halogen group Chemical group 0.000 claims description 36
• 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 35
• 239000003085 diluting agent Substances 0.000 claims description 35
• XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 34
• 239000001257 hydrogen Substances 0.000 claims description 34
• 229910052717 sulfur Chemical group 0.000 claims description 34
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 33
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 33
• 229920006395 saturated elastomer Polymers 0.000 claims description 33
• 239000011593 sulfur Chemical group 0.000 claims description 33
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 31
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 30
• 229940079593 drug Drugs 0.000 claims description 29
• 238000002360 preparation method Methods 0.000 claims description 29
• 229910052799 carbon Inorganic materials 0.000 claims description 28
• 125000005842 heteroatom Chemical group 0.000 claims description 28
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 28
• 150000001412 amines Chemical class 0.000 claims description 27
• 239000000126 substance Substances 0.000 claims description 26
• 125000004432 carbon atom Chemical group C* 0.000 claims description 24
• 206010012601 diabetes mellitus Diseases 0.000 claims description 23
• 125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 20
• 125000004414 alkyl thio group Chemical group 0.000 claims description 20
• 125000001153 fluoro group Chemical group F* 0.000 claims description 20
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 19
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 19
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 18
• 239000002552 dosage form Substances 0.000 claims description 17
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
• 230000005764 inhibitory process Effects 0.000 claims description 16
• 229910052727 yttrium Inorganic materials 0.000 claims description 16
• 208000008589 Obesity Diseases 0.000 claims description 14
• 125000003282 alkyl amino group Chemical group 0.000 claims description 14
• 150000002431 hydrogen Chemical class 0.000 claims description 14
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 14
• 235000020824 obesity Nutrition 0.000 claims description 14
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 13
• 150000001721 carbon Chemical group 0.000 claims description 13
• 229910052720 vanadium Inorganic materials 0.000 claims description 13
• 208000031226 Hyperlipidaemia Diseases 0.000 claims description 12
• 208000001132 Osteoporosis Diseases 0.000 claims description 12
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 12
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 12
• 125000002619 bicyclic group Chemical group 0.000 claims description 11
• 239000000562 conjugate Substances 0.000 claims description 11
• 229960001915 hexamidine Drugs 0.000 claims description 11
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 10
• 206010020772 Hypertension Diseases 0.000 claims description 10
• 208000001145 Metabolic Syndrome Diseases 0.000 claims description 10
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
• 230000007721 medicinal effect Effects 0.000 claims description 10
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 10
• 208000024891 symptom Diseases 0.000 claims description 10
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 9
• 208000002249 Diabetes Complications Diseases 0.000 claims description 9
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
• 125000000623 heterocyclic group Chemical group 0.000 claims description 9
• NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 9
• 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 9
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 8
• 206010022489 Insulin Resistance Diseases 0.000 claims description 8
• 229940086609 Lipase inhibitor Drugs 0.000 claims description 8
• PCZOHLXUXFIOCF-UHFFFAOYSA-N Monacolin X Natural products C12C(OC(=O)C(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 PCZOHLXUXFIOCF-UHFFFAOYSA-N 0.000 claims description 8
• 125000002837 carbocyclic group Chemical group 0.000 claims description 8
• 229960004844 lovastatin Drugs 0.000 claims description 8
• PCZOHLXUXFIOCF-BXMDZJJMSA-N lovastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 PCZOHLXUXFIOCF-BXMDZJJMSA-N 0.000 claims description 8
• QLJODMDSTUBWDW-UHFFFAOYSA-N lovastatin hydroxy acid Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(C)C=C21 QLJODMDSTUBWDW-UHFFFAOYSA-N 0.000 claims description 8
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
• 125000004149 thio group Chemical group *S* 0.000 claims description 8
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 8
• HSINOMROUCMIEA-FGVHQWLLSA-N (2s,4r)-4-[(3r,5s,6r,7r,8s,9s,10s,13r,14s,17r)-6-ethyl-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-methylpentanoic acid Chemical compound C([C@@]12C)C[C@@H](O)C[C@H]1[C@@H](CC)[C@@H](O)[C@@H]1[C@@H]2CC[C@]2(C)[C@@H]([C@H](C)C[C@H](C)C(O)=O)CC[C@H]21 HSINOMROUCMIEA-FGVHQWLLSA-N 0.000 claims description 7
• 239000005711 Benzoic acid Substances 0.000 claims description 7
• 208000035150 Hypercholesterolemia Diseases 0.000 claims description 7
• 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims description 7
• 238000010521 absorption reaction Methods 0.000 claims description 7
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 7
• 125000004429 atom Chemical group 0.000 claims description 7
• 239000003613 bile acid Substances 0.000 claims description 7
• 208000029078 coronary artery disease Diseases 0.000 claims description 7
• 238000006467 substitution reaction Methods 0.000 claims description 7
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 7
• 229940122502 Cholesterol absorption inhibitor Drugs 0.000 claims description 6
• 229940122498 Gene expression inhibitor Drugs 0.000 claims description 6
• 208000002705 Glucose Intolerance Diseases 0.000 claims description 6
• 206010019280 Heart failures Diseases 0.000 claims description 6
• 206010033307 Overweight Diseases 0.000 claims description 6
• 125000003277 amino group Chemical group 0.000 claims description 6
• 239000003937 drug carrier Substances 0.000 claims description 6
• 125000000524 functional group Chemical group 0.000 claims description 6
• 208000006575 hypertriglyceridemia Diseases 0.000 claims description 6
• 201000009104 prediabetes syndrome Diseases 0.000 claims description 6
• 230000028327 secretion Effects 0.000 claims description 6
• 206010007559 Cardiac failure congestive Diseases 0.000 claims description 5
• 206010061218 Inflammation Diseases 0.000 claims description 5
• 125000003342 alkenyl group Chemical group 0.000 claims description 5
• 150000003973 alkyl amines Chemical class 0.000 claims description 5
• 230000004054 inflammatory process Effects 0.000 claims description 5
• KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 claims description 5
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
• 150000003254 radicals Chemical group 0.000 claims description 5
• 206010060378 Hyperinsulinaemia Diseases 0.000 claims description 4
• 102000004316 Oxidoreductases Human genes 0.000 claims description 4
• 108090000854 Oxidoreductases Proteins 0.000 claims description 4
• 208000007536 Thrombosis Diseases 0.000 claims description 4
• 239000003963 antioxidant agent Substances 0.000 claims description 4
• 230000003451 hyperinsulinaemic effect Effects 0.000 claims description 4
• 201000008980 hyperinsulinism Diseases 0.000 claims description 4
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
• 230000036961 partial effect Effects 0.000 claims description 4
• 239000004575 stone Chemical group 0.000 claims description 4
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 4
• 125000003944 tolyl group Chemical group 0.000 claims description 4
• 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 claims description 3
• 206010021024 Hypolipidaemia Diseases 0.000 claims description 3
• 230000003078 antioxidant effect Effects 0.000 claims description 3
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 3
• 125000005567 fluorenylene group Chemical group 0.000 claims description 3
• 208000029498 hypoalphalipoproteinemia Diseases 0.000 claims description 3
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
• 125000001424 substituent group Chemical group 0.000 claims description 3
• NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 2
• SCVJRXQHFJXZFZ-KVQBGUIXSA-N 2-amino-9-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3h-purine-6-thione Chemical compound C1=2NC(N)=NC(=S)C=2N=CN1[C@H]1C[C@H](O)[C@@H](CO)O1 SCVJRXQHFJXZFZ-KVQBGUIXSA-N 0.000 claims description 2
• 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 2
• 229940123320 Cyclase inhibitor Drugs 0.000 claims description 2
• 235000021355 Stearic acid Nutrition 0.000 claims description 2
• 150000001335 aliphatic alkanes Chemical class 0.000 claims description 2
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 2
• 239000002738 chelating agent Substances 0.000 claims description 2
• 239000003456 ion exchange resin Substances 0.000 claims description 2
• 229920003303 ion-exchange polymer Polymers 0.000 claims description 2
• QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 2
• OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims description 2
• 125000003386 piperidinyl group Chemical group 0.000 claims description 2
• 235000019260 propionic acid Nutrition 0.000 claims description 2
• 239000008117 stearic acid Substances 0.000 claims description 2
• 125000004354 sulfur functional group Chemical group 0.000 claims description 2
• BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Substances OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 5
• 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 3
• OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical class COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims 2
• 235000019253 formic acid Nutrition 0.000 claims 2
• 125000004043 oxo group Chemical group O=* 0.000 claims 2
• DJXBOEOWRNXBIT-UHFFFAOYSA-N 2-methyl-2-[3-[1-(4-propan-2-ylphenoxy)carbonylpiperidin-3-yl]phenoxy]propanoic acid Chemical compound C1=CC(C(C)C)=CC=C1OC(=O)N1CC(C=2C=C(OC(C)(C)C(O)=O)C=CC=2)CCC1 DJXBOEOWRNXBIT-UHFFFAOYSA-N 0.000 claims 1
• UVILUUWUTHCPSG-SFHVURJKSA-N 2-methyl-5-[(3r)-1-[2-[4-(trifluoromethyl)phenyl]ethoxycarbonyl]piperidin-3-yl]benzoic acid Chemical compound C1=C(C(O)=O)C(C)=CC=C1[C@@H]1CN(C(=O)OCCC=2C=CC(=CC=2)C(F)(F)F)CCC1 UVILUUWUTHCPSG-SFHVURJKSA-N 0.000 claims 1
• CHYZNDMDRQIKKJ-QGZVFWFLSA-N 2-methyl-5-[(3s)-1-[[4-(trifluoromethyl)phenyl]methoxycarbonyl]piperidin-3-yl]benzoic acid Chemical compound C1=C(C(O)=O)C(C)=CC=C1[C@H]1CN(C(=O)OCC=2C=CC(=CC=2)C(F)(F)F)CCC1 CHYZNDMDRQIKKJ-QGZVFWFLSA-N 0.000 claims 1
• 125000004810 2-methylpropylene group Chemical group [H]C([H])([H])C([H])(C([H])([H])[*:2])C([H])([H])[*:1] 0.000 claims 1
• KEWSCDNULKOKTG-UHFFFAOYSA-N 4-cyano-4-ethylsulfanylcarbothioylsulfanylpentanoic acid Chemical compound CCSC(=S)SC(C)(C#N)CCC(O)=O KEWSCDNULKOKTG-UHFFFAOYSA-N 0.000 claims 1
• 125000002528 4-isopropyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
• OQLZINXFSUDMHM-UHFFFAOYSA-N Acetamidine Chemical compound CC(N)=N OQLZINXFSUDMHM-UHFFFAOYSA-N 0.000 claims 1
• VEDTXTNSFWUXGQ-UHFFFAOYSA-N Carbophenothion Chemical group CCOP(=S)(OCC)SCSC1=CC=C(Cl)C=C1 VEDTXTNSFWUXGQ-UHFFFAOYSA-N 0.000 claims 1
• 102100037637 Cholesteryl ester transfer protein Human genes 0.000 claims 1
• 108010022535 Farnesyl-Diphosphate Farnesyltransferase Proteins 0.000 claims 1
• 101000880514 Homo sapiens Cholesteryl ester transfer protein Proteins 0.000 claims 1
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• 125000002877 alkyl aryl group Chemical group 0.000 claims 1
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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 1
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• HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 abstract description 84
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