TW200305403A - Compounds that modulate PPAR activity - Google Patents

Info

Publication number

TW200305403A

TW200305403A TW092104790A TW92104790A TW200305403A TW 200305403 A TW200305403 A TW 200305403A TW 092104790 A TW092104790 A TW 092104790A TW 92104790 A TW92104790 A TW 92104790A TW 200305403 A TW200305403 A TW 200305403A

Authority

TW

Taiwan

Prior art keywords

compound

methyl

hydrogen

alkyl

acid

Prior art date

2002-03-07

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 475
• 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 title abstract description 12
• 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 title abstract description 12
• 230000000694 effects Effects 0.000 title abstract description 11
• 238000000034 method Methods 0.000 claims abstract description 33
• 150000003839 salts Chemical class 0.000 claims abstract description 17
• 208000035150 Hypercholesterolemia Diseases 0.000 claims abstract description 12
• 239000003814 drug Substances 0.000 claims abstract description 10
• -1 methoxy, ethoxy, isopropoxy, n-propoxy Chemical group 0.000 claims description 141
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 102
• 125000000217 alkyl group Chemical group 0.000 claims description 97
• 239000001257 hydrogen Substances 0.000 claims description 92
• 229910052739 hydrogen Inorganic materials 0.000 claims description 92
• 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 48
• 150000002431 hydrogen Chemical class 0.000 claims description 48
• 125000003118 aryl group Chemical group 0.000 claims description 36
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 31
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 28
• 239000002253 acid Substances 0.000 claims description 27
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 27
• 125000000304 alkynyl group Chemical group 0.000 claims description 23
• 125000003342 alkenyl group Chemical group 0.000 claims description 21
• 125000003545 alkoxy group Chemical group 0.000 claims description 16
• 229910052799 carbon Inorganic materials 0.000 claims description 16
• 229910052736 halogen Inorganic materials 0.000 claims description 15
• 150000002367 halogens Chemical class 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 15
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 13
• 238000006243 chemical reaction Methods 0.000 claims description 11
• 125000005842 heteroatom Chemical group 0.000 claims description 11
• 125000001072 heteroaryl group Chemical group 0.000 claims description 10
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 9
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 9
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 8
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
• 239000000126 substance Substances 0.000 claims description 8
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 7
• 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 7
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 6
• 125000001318 4-trifluoromethylbenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])*)C(F)(F)F 0.000 claims description 6
• 206010003210 Arteriosclerosis Diseases 0.000 claims description 6
• 208000011775 arteriosclerosis disease Diseases 0.000 claims description 6
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 6
• 125000003107 substituted aryl group Chemical group 0.000 claims description 6
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 5
• 125000001188 haloalkyl group Chemical group 0.000 claims description 5
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
• 239000008194 pharmaceutical composition Substances 0.000 claims description 5
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• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
• 230000002265 prevention Effects 0.000 claims description 4
• 125000005843 halogen group Chemical group 0.000 claims description 3
• 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 claims description 3
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
• 125000004646 sulfenyl group Chemical group S(*)* 0.000 claims description 3
• 229910002651 NO3 Inorganic materials 0.000 claims description 2
• 210000004268 dentin Anatomy 0.000 claims description 2
• NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 2
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• 239000003279 phenylacetic acid Substances 0.000 claims description 2
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• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 2
• NITGRSXVWGEDCP-UHFFFAOYSA-N 2-[4-(trifluoromethyl)phenyl]-1,3-oxazole Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=NC=CO1 NITGRSXVWGEDCP-UHFFFAOYSA-N 0.000 claims 1
• PDZADHWORZUTBL-UHFFFAOYSA-N 2-phenyl-2-(1H-pyrrol-2-yl)propanoic acid Chemical compound C1(=CC=CC=C1)C(C(=O)O)(C)C=1NC=CC1 PDZADHWORZUTBL-UHFFFAOYSA-N 0.000 claims 1
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• 125000004079 stearyl 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])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])[H] 0.000 claims 1
• 239000000203 mixture Substances 0.000 abstract description 59
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• 238000002360 preparation method Methods 0.000 description 141
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical class CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 122
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 109
• 238000005481 NMR spectroscopy Methods 0.000 description 78
• 235000019439 ethyl acetate Nutrition 0.000 description 53
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 51
• 239000000047 product Substances 0.000 description 40
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 38
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• 229910001868 water Inorganic materials 0.000 description 38
• 229960000583 acetic acid Drugs 0.000 description 37
• 239000000243 solution Substances 0.000 description 37
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 36
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 32
• 239000007787 solid Substances 0.000 description 29
• 239000011541 reaction mixture Substances 0.000 description 26
• 238000003786 synthesis reaction Methods 0.000 description 25
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
• KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 22
• 230000015572 biosynthetic process Effects 0.000 description 22
• 229940125904 compound 1 Drugs 0.000 description 21
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• 235000019198 oils Nutrition 0.000 description 21
• 239000002904 solvent Substances 0.000 description 21
• XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 20
• 239000010410 layer Substances 0.000 description 20
• 239000012267 brine Substances 0.000 description 19
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 19
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• 239000007788 liquid Substances 0.000 description 18
• 238000003818 flash chromatography Methods 0.000 description 17
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
• 238000000746 purification Methods 0.000 description 15
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• 229910052757 nitrogen Inorganic materials 0.000 description 14
• 101150041968 CDC13 gene Proteins 0.000 description 13
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• 238000010992 reflux Methods 0.000 description 13
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• 238000004587 chromatography analysis Methods 0.000 description 12
• 239000012043 crude product Substances 0.000 description 12
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• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
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• GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 8
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