JP2006515838A - ファルネソイドｘ受容体アゴニスト - Google Patents
ファルネソイドｘ受容体アゴニスト Download PDFInfo
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- JP2006515838A JP2006515838A JP2004555406A JP2004555406A JP2006515838A JP 2006515838 A JP2006515838 A JP 2006515838A JP 2004555406 A JP2004555406 A JP 2004555406A JP 2004555406 A JP2004555406 A JP 2004555406A JP 2006515838 A JP2006515838 A JP 2006515838A
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- methyl
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- 229940121360 farnesoid X receptor (fxr) agonists Drugs 0.000 title abstract description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 386
- 238000000034 method Methods 0.000 claims abstract description 72
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 29
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 89
- 238000011282 treatment Methods 0.000 claims description 63
- 230000002265 prevention Effects 0.000 claims description 55
- 125000000217 alkyl group Chemical group 0.000 claims description 47
- 102100038495 Bile acid receptor Human genes 0.000 claims description 44
- 101000603876 Homo sapiens Bile acid receptor Proteins 0.000 claims description 44
- 206010016654 Fibrosis Diseases 0.000 claims description 32
- 239000003814 drug Substances 0.000 claims description 32
- 230000004761 fibrosis Effects 0.000 claims description 31
- 238000004519 manufacturing process Methods 0.000 claims description 27
- 125000003342 alkenyl group Chemical group 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 23
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 19
- 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 claims description 18
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 18
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 18
- 125000001072 heteroaryl group Chemical group 0.000 claims description 18
- 210000000056 organ Anatomy 0.000 claims description 18
- 239000012039 electrophile Substances 0.000 claims description 17
- 125000000623 heterocyclic group Chemical group 0.000 claims description 17
- 230000001404 mediated effect Effects 0.000 claims description 16
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 15
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 15
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 14
- 239000012453 solvate Substances 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 125000006239 protecting group Chemical group 0.000 claims description 12
- 208000024891 symptom Diseases 0.000 claims description 12
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 10
- 206010008635 Cholestasis Diseases 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 150000003626 triacylglycerols Chemical class 0.000 claims description 10
- 125000000304 alkynyl group Chemical group 0.000 claims description 9
- 235000012000 cholesterol Nutrition 0.000 claims description 9
- 201000001320 Atherosclerosis Diseases 0.000 claims description 8
- 208000035150 Hypercholesterolemia Diseases 0.000 claims description 8
- 238000010511 deprotection reaction Methods 0.000 claims description 6
- 239000003085 diluting agent Substances 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 238000002560 therapeutic procedure Methods 0.000 claims description 5
- 125000004450 alkenylene group Chemical group 0.000 claims description 4
- 230000002152 alkylating effect Effects 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 238000005660 chlorination reaction Methods 0.000 claims description 4
- 230000008707 rearrangement Effects 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- 230000009467 reduction Effects 0.000 claims description 3
- 125000001475 halogen functional group Chemical group 0.000 claims 5
- 238000002360 preparation method Methods 0.000 abstract description 6
- 230000015572 biosynthetic process Effects 0.000 description 103
- -1 2,6-dichlorophenyl Chemical group 0.000 description 100
- 238000003786 synthesis reaction Methods 0.000 description 100
- 239000007858 starting material Substances 0.000 description 98
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 63
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 61
- 229940095102 methyl benzoate Drugs 0.000 description 53
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 42
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 41
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
- 239000000203 mixture Substances 0.000 description 38
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 36
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 35
- 239000000243 solution Substances 0.000 description 33
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 30
- 238000006243 chemical reaction Methods 0.000 description 29
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- 235000002639 sodium chloride Nutrition 0.000 description 25
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 22
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 21
- 239000003613 bile acid Substances 0.000 description 19
- 125000005843 halogen group Chemical group 0.000 description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- 239000005711 Benzoic acid Substances 0.000 description 18
- 235000010233 benzoic acid Nutrition 0.000 description 18
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
- 125000001424 substituent group Chemical group 0.000 description 17
- 208000019425 cirrhosis of liver Diseases 0.000 description 16
- 239000002904 solvent Substances 0.000 description 16
- 210000004027 cell Anatomy 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 241000124008 Mammalia Species 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 210000004185 liver Anatomy 0.000 description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- 239000012267 brine Substances 0.000 description 12
- 201000010099 disease Diseases 0.000 description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 12
- 239000000843 powder Substances 0.000 description 12
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 11
- 239000003446 ligand Substances 0.000 description 11
- 239000012044 organic layer Substances 0.000 description 11
- 239000004480 active ingredient Substances 0.000 description 10
- 239000002585 base Substances 0.000 description 10
- 239000003112 inhibitor Substances 0.000 description 9
- 229910000027 potassium carbonate Inorganic materials 0.000 description 9
- 238000010898 silica gel chromatography Methods 0.000 description 9
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 9
- 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 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 8
- 238000009472 formulation Methods 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- 108090000765 processed proteins & peptides Proteins 0.000 description 8
- 239000011734 sodium Substances 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 239000003826 tablet Substances 0.000 description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 7
- 239000003153 chemical reaction reagent Substances 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 210000003491 skin Anatomy 0.000 description 7
- YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 description 6
- 0 Cc1c(C)[o]c(*)c1C*c(c(C)c1)ccc1O Chemical compound Cc1c(C)[o]c(*)c1C*c(c(C)c1)ccc1O 0.000 description 6
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 6
- 239000000872 buffer Substances 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
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- 239000000314 lubricant Substances 0.000 description 6
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- 102000005962 receptors Human genes 0.000 description 6
- 108020003175 receptors Proteins 0.000 description 6
- 238000010561 standard procedure Methods 0.000 description 6
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- 201000004624 Dermatitis Diseases 0.000 description 5
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- 101001062849 Homo sapiens Gastrotropin Proteins 0.000 description 5
- 108010090804 Streptavidin Proteins 0.000 description 5
- 239000000556 agonist Substances 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 description 5
- 230000014509 gene expression Effects 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000000523 sample Substances 0.000 description 5
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 5
- 229910000342 sodium bisulfate Inorganic materials 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
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- JMDLBQMKBBJSKK-UHFFFAOYSA-N 4-(chloromethyl)-3-(2,6-dichlorophenyl)-5-propan-2-yl-1,2-oxazole Chemical compound ClCC1=C(C(C)C)ON=C1C1=C(Cl)C=CC=C1Cl JMDLBQMKBBJSKK-UHFFFAOYSA-N 0.000 description 4
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- YRRMSEOBVQHNMJ-UHFFFAOYSA-N 1-[4-[[3-(2,6-dichlorophenyl)-5-propan-2-yl-1,2-oxazol-4-yl]methoxy]-2-methylphenyl]ethanone Chemical compound CC(C)C=1ON=C(C=2C(=CC=CC=2Cl)Cl)C=1COC1=CC=C(C(C)=O)C(C)=C1 YRRMSEOBVQHNMJ-UHFFFAOYSA-N 0.000 description 3
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- OYSSSRDSHNWHFQ-UHFFFAOYSA-N 4-[[3-chloro-4-(chloromethyl)phenoxy]methyl]-3-(2,6-dichlorophenyl)-5-propan-2-yl-1,2-oxazole Chemical compound CC(C)C=1ON=C(C=2C(=CC=CC=2Cl)Cl)C=1COC1=CC=C(CCl)C(Cl)=C1 OYSSSRDSHNWHFQ-UHFFFAOYSA-N 0.000 description 3
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- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
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Classifications
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- C07D261/08—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more 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
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- 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
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- 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
- C07D417/12—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 linked by a chain containing hetero atoms as chain links
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| US42837402P | 2002-11-22 | 2002-11-22 | |
| PCT/US2003/035808 WO2004048349A1 (en) | 2002-11-22 | 2003-11-12 | Farnesoid x receptor agonists |
Publications (2)
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| JP2006515838A true JP2006515838A (ja) | 2006-06-08 |
| JP2006515838A5 JP2006515838A5 (https=) | 2006-12-14 |
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| EP (1) | EP1562915A1 (https=) |
| JP (1) | JP2006515838A (https=) |
| AU (1) | AU2003290700A1 (https=) |
| WO (1) | WO2004048349A1 (https=) |
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| JP2013502389A (ja) * | 2009-08-19 | 2013-01-24 | フェネックス ファーマシューティカルス アーゲー | 新規のｆｘｒ（ｎｒ１ｈ４）結合性及び活性調節性化合物 |
| JP2021530535A (ja) * | 2018-07-17 | 2021-11-11 | バー ファーマシューティカルズ ソチエタ レスポンサビリタ リミタータ | Ｆｘｒ受容体アゴニストとしてのイソオキサゾール |
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- 2003-11-12 WO PCT/US2003/035808 patent/WO2004048349A1/en not_active Ceased
- 2003-11-12 JP JP2004555406A patent/JP2006515838A/ja active Pending
- 2003-11-12 EP EP03783282A patent/EP1562915A1/en not_active Withdrawn
- 2003-11-12 US US10/535,228 patent/US7319109B2/en not_active Expired - Fee Related
- 2003-11-12 AU AU2003290700A patent/AU2003290700A1/en not_active Abandoned
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| JPH11263775A (ja) * | 1997-09-08 | 1999-09-28 | Sankyo Co Ltd | ヒドロキシアニリン誘導体 |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2012506386A (ja) * | 2008-10-21 | 2012-03-15 | メタボレックス， インコーポレイテッド | アリールｇｐｒ１２０受容体アゴニストおよびその使用 |
| JP2013502389A (ja) * | 2009-08-19 | 2013-01-24 | フェネックス ファーマシューティカルス アーゲー | 新規のｆｘｒ（ｎｒ１ｈ４）結合性及び活性調節性化合物 |
| JP2021530535A (ja) * | 2018-07-17 | 2021-11-11 | バー ファーマシューティカルズ ソチエタ レスポンサビリタ リミタータ | Ｆｘｒ受容体アゴニストとしてのイソオキサゾール |
| JP7629846B2 (ja) | 2018-07-17 | 2025-02-14 | バー ファーマシューティカルズ ソチエタ レスポンサビリタ リミタータ | Ｆｘｒ受容体アゴニストとしてのイソオキサゾール |
Also Published As
| Publication number | Publication date |
|---|---|
| US7319109B2 (en) | 2008-01-15 |
| AU2003290700A1 (en) | 2004-06-18 |
| US20060258725A1 (en) | 2006-11-16 |
| EP1562915A1 (en) | 2005-08-17 |
| WO2004048349A1 (en) | 2004-06-10 |
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