JP2007532563A5

JP2007532563A5 -

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Publication number: JP2007532563A5
Authority: JP; Japan
Prior art keywords: phenyl; compound; group; methyl; optionally substituted
Prior art date: 2005-04-07
Legal status : Pending

Application number

JP2007507492A

Other languages

English (en)

Japanese (ja)

Other versions

JP2007532563A (ja

Filing date

2005-04-07

Publication date

2011-03-10

2005-04-07 Application filed filed Critical

2005-04-07 Priority claimed from PCT/US2005/011751 external-priority patent/WO2005115983A1/en

2007-11-15 Publication of JP2007532563A publication Critical patent/JP2007532563A/ja

2011-03-10 Publication of JP2007532563A5 publication Critical patent/JP2007532563A5/ja

Status Pending legal-status Critical Current

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150000001875 compounds Chemical class 0.000 claims description 431
-1 lower perhaloalkyl Chemical group 0.000 claims description 85
125000000217 alkyl group Chemical group 0.000 claims description 76
229910052739 hydrogen Inorganic materials 0.000 claims description 54
239000001257 hydrogen Substances 0.000 claims description 54
229910052799 carbon Inorganic materials 0.000 claims description 49
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 46
150000002431 hydrogen Chemical class 0.000 claims description 44
238000011282 treatment Methods 0.000 claims description 44
229910052736 halogen Inorganic materials 0.000 claims description 41
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 40
150000002367 halogens Chemical class 0.000 claims description 39
125000004404 heteroalkyl group Chemical group 0.000 claims description 38
125000003545 alkoxy group Chemical group 0.000 claims description 37
201000010099 disease Diseases 0.000 claims description 34
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 30
125000001072 heteroaryl group Chemical group 0.000 claims description 26
125000003118 aryl group Chemical group 0.000 claims description 24
229910052757 nitrogen Inorganic materials 0.000 claims description 23
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 22
125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 21
150000002148 esters Chemical class 0.000 claims description 18
150000003839 salts Chemical class 0.000 claims description 18
125000004093 cyano group Chemical group *C#N 0.000 claims description 17
150000001408 amides Chemical class 0.000 claims description 16
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239000000651 prodrug Substances 0.000 claims description 14
229940002612 prodrug Drugs 0.000 claims description 14
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XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 13
239000002207 metabolite Substances 0.000 claims description 11
239000012453 solvate Substances 0.000 claims description 11
125000000304 alkynyl group Chemical group 0.000 claims description 10
238000002560 therapeutic procedure Methods 0.000 claims description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
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208000001145 Metabolic Syndrome Diseases 0.000 claims description 8
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201000010390 abdominal obesity-metabolic syndrome 1 Diseases 0.000 claims description 8
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150000001721 carbon Chemical group 0.000 claims description 7
PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 7
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
125000003107 substituted aryl group Chemical group 0.000 claims description 7
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125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
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125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
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230000004054 inflammatory process Effects 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
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125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 4
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125000001931 aliphatic group Chemical group 0.000 claims description 3
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125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
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125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
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125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
239000003085 diluting agent Substances 0.000 claims description 2
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239000000243 solution Substances 0.000 description 202
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RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 89
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 88
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239000000047 product Substances 0.000 description 42
239000013067 intermediate product Substances 0.000 description 41
238000003756 stirring Methods 0.000 description 39
FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 description 38
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 37
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 37
239000012267 brine Substances 0.000 description 36
239000012044 organic layer Substances 0.000 description 36
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 34
210000004027 cell Anatomy 0.000 description 34
238000006243 chemical reaction Methods 0.000 description 34
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UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 24
238000004440 column chromatography Methods 0.000 description 24
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 23
238000001914 filtration Methods 0.000 description 23
125000001424 substituent group Chemical group 0.000 description 23
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 22
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
238000010992 reflux Methods 0.000 description 21
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
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239000012043 crude product Substances 0.000 description 19
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
125000004435 hydrogen atom Chemical group [H]* 0.000 description 18
229940124530 sulfonamide Drugs 0.000 description 18
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 17
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 16
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
238000004458 analytical method Methods 0.000 description 16
230000027455 binding Effects 0.000 description 16
230000015572 biosynthetic process Effects 0.000 description 16
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239000012038 nucleophile Substances 0.000 description 14
108010015181 PPAR delta Proteins 0.000 description 13
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239000000126 substance Substances 0.000 description 13
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VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 12
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
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125000000753 cycloalkyl group Chemical group 0.000 description 12
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RZKVXRPQKFTWBN-UHFFFAOYSA-N methyl 2-(3-chlorosulfonyl-5-methylphenyl)acetate Chemical compound COC(=O)CC1=CC(C)=CC(S(Cl)(=O)=O)=C1 RZKVXRPQKFTWBN-UHFFFAOYSA-N 0.000 description 8
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BPDSHHYIJSBWPL-UHFFFAOYSA-N methyl 2-(3-chlorosulfonylphenyl)acetate Chemical compound COC(=O)CC1=CC=CC(S(Cl)(=O)=O)=C1 BPDSHHYIJSBWPL-UHFFFAOYSA-N 0.000 description 7
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QFQRXCNZWQRTNP-XMMPIXPASA-N methyl (2r)-1-[4-methyl-3-[2-[(4-nitrophenyl)methoxy]-2-oxoethyl]phenyl]sulfonyl-4-[5-(trifluoromethyl)pyridin-2-yl]piperazine-2-carboxylate Chemical compound C([C@@H]1C(=O)OC)N(C=2N=CC(=CC=2)C(F)(F)F)CCN1S(=O)(=O)C(C=1)=CC=C(C)C=1CC(=O)OCC1=CC=C([N+]([O-])=O)C=C1 QFQRXCNZWQRTNP-XMMPIXPASA-N 0.000 description 1
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MXQWKXUNLITQMM-UHFFFAOYSA-N methyl 2-(3-amino-5-bromophenyl)acetate Chemical compound COC(=O)CC1=CC(N)=CC(Br)=C1 MXQWKXUNLITQMM-UHFFFAOYSA-N 0.000 description 1
LOESFNNSRXLPMV-UHFFFAOYSA-N methyl 2-(3-bromo-5-nitrophenyl)acetate Chemical compound COC(=O)CC1=CC(Br)=CC([N+]([O-])=O)=C1 LOESFNNSRXLPMV-UHFFFAOYSA-N 0.000 description 1
MKDNECXSMWRJRK-UHFFFAOYSA-N methyl 2-(3-chlorosulfonyl-2,6-difluorophenyl)acetate Chemical compound COC(=O)CC1=C(F)C=CC(S(Cl)(=O)=O)=C1F MKDNECXSMWRJRK-UHFFFAOYSA-N 0.000 description 1
LCRRPGDWZDWEOS-UHFFFAOYSA-N methyl 2-[2-hydroxy-5-[4-[5-(trifluoromethyl)pyridin-2-yl]piperazin-1-yl]sulfonylphenyl]acetate Chemical compound C1=C(O)C(CC(=O)OC)=CC(S(=O)(=O)N2CCN(CC2)C=2N=CC(=CC=2)C(F)(F)F)=C1 LCRRPGDWZDWEOS-UHFFFAOYSA-N 0.000 description 1
VPVOJZNOALAGDI-UHFFFAOYSA-N methyl 2-[2-methoxy-5-[4-[5-(trifluoromethyl)pyridin-2-yl]piperazin-1-yl]sulfonylphenyl]acetate Chemical compound C1=C(OC)C(CC(=O)OC)=CC(S(=O)(=O)N2CCN(CC2)C=2N=CC(=CC=2)C(F)(F)F)=C1 VPVOJZNOALAGDI-UHFFFAOYSA-N 0.000 description 1
SKHKECXHXYFZEH-UHFFFAOYSA-N methyl 2-[2-methyl-5-[2-methyl-4-[5-(trifluoromethyl)pyridin-2-yl]piperazin-1-yl]sulfonylphenyl]acetate Chemical compound C1=C(C)C(CC(=O)OC)=CC(S(=O)(=O)N2C(CN(CC2)C=2N=CC(=CC=2)C(F)(F)F)C)=C1 SKHKECXHXYFZEH-UHFFFAOYSA-N 0.000 description 1
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ZWDIVYGJFPJWJO-UHFFFAOYSA-N methyl 2-[3-(bromomethyl)-5-[4-[4-(trifluoromethyl)phenyl]piperazin-1-yl]sulfonylphenyl]acetate Chemical compound COC(=O)CC1=CC(CBr)=CC(S(=O)(=O)N2CCN(CC2)C=2C=CC(=CC=2)C(F)(F)F)=C1 ZWDIVYGJFPJWJO-UHFFFAOYSA-N 0.000 description 1
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JP2007507492A 2004-04-07 2005-04-07 Ｐｐａｒの調整剤としてのアリールスルホンアミド及びスルホニル化合物ならびに代謝障害を治療する方法 Pending JP2007532563A (ja)