JP2006509022A5 - - Google Patents
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- Publication number
- JP2006509022A5 JP2006509022A5 JP2004558041A JP2004558041A JP2006509022A5 JP 2006509022 A5 JP2006509022 A5 JP 2006509022A5 JP 2004558041 A JP2004558041 A JP 2004558041A JP 2004558041 A JP2004558041 A JP 2004558041A JP 2006509022 A5 JP2006509022 A5 JP 2006509022A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- oxo
- isobutylphenyl
- methyl
- isobutyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- -1 C 1 -C 4 - acyloxy Chemical group 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 11
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
- 229960001760 dimethyl sulfoxide Drugs 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 3
- MDDHXQWPMRKRBD-GFCCVEGCSA-N (2r)-2-[4-(2-methylpropyl)phenyl]pentan-3-one Chemical compound CCC(=O)[C@H](C)C1=CC=C(CC(C)C)C=C1 MDDHXQWPMRKRBD-GFCCVEGCSA-N 0.000 claims description 2
- UUTXGQUXLKVJCL-QGZVFWFLSA-N (2r)-3-oxo-2-[4-(3-oxo-1h-isoindol-2-yl)phenyl]pentanamide Chemical compound C1=CC([C@@H](C(N)=O)C(=O)CC)=CC=C1N1C(=O)C2=CC=CC=C2C1 UUTXGQUXLKVJCL-QGZVFWFLSA-N 0.000 claims description 2
- MKJYJOWDXMMVHD-KRWDZBQOSA-N (2r)-3-oxo-2-[4-(3-oxo-1h-isoindol-2-yl)phenyl]pentanenitrile Chemical compound C1=CC([C@H](C#N)C(=O)CC)=CC=C1N1C(=O)C2=CC=CC=C2C1 MKJYJOWDXMMVHD-KRWDZBQOSA-N 0.000 claims description 2
- SGZQOTMMVLQDFL-LBPRGKRZSA-N (3r)-3-(3-benzoylphenyl)butan-2-one Chemical compound CC(=O)[C@H](C)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 SGZQOTMMVLQDFL-LBPRGKRZSA-N 0.000 claims description 2
- OIGZBRIFCOWGTP-MRXNPFEDSA-N (3r)-3-[4-(2-methylpropyl)phenyl]-1-phenylbutan-2-one Chemical compound C1=CC(CC(C)C)=CC=C1[C@@H](C)C(=O)CC1=CC=CC=C1 OIGZBRIFCOWGTP-MRXNPFEDSA-N 0.000 claims description 2
- VOYZJYGIHFRNAG-NSHDSACASA-N (3r)-3-[4-(2-methylpropyl)phenyl]butan-2-one Chemical compound CC(C)CC1=CC=C([C@@H](C)C(C)=O)C=C1 VOYZJYGIHFRNAG-NSHDSACASA-N 0.000 claims description 2
- SGZQOTMMVLQDFL-GFCCVEGCSA-N (3s)-3-(3-benzoylphenyl)butan-2-one Chemical compound CC(=O)[C@@H](C)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 SGZQOTMMVLQDFL-GFCCVEGCSA-N 0.000 claims description 2
- VOYZJYGIHFRNAG-LLVKDONJSA-N (3s)-3-[4-(2-methylpropyl)phenyl]butan-2-one Chemical compound CC(C)CC1=CC=C([C@H](C)C(C)=O)C=C1 VOYZJYGIHFRNAG-LLVKDONJSA-N 0.000 claims description 2
- SMPOYUDSLNFLFV-QGZVFWFLSA-N (4r)-4-[4-(2-methylpropyl)phenyl]-1-phenylpentan-3-one Chemical compound C1=CC(CC(C)C)=CC=C1[C@@H](C)C(=O)CCC1=CC=CC=C1 SMPOYUDSLNFLFV-QGZVFWFLSA-N 0.000 claims description 2
- GOMZQENQNXLCMQ-MRXNPFEDSA-N (4r)-4-[4-(2-methylpropyl)phenyl]-1-pyridin-3-ylpentan-3-one Chemical compound C1=CC(CC(C)C)=CC=C1[C@@H](C)C(=O)CCC1=CC=CN=C1 GOMZQENQNXLCMQ-MRXNPFEDSA-N 0.000 claims description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- QQBQJFKONBDWOS-UHFFFAOYSA-N 4-[4-(2-methylpropyl)phenyl]-3-oxopentanoic acid Chemical compound CC(C)CC1=CC=C(C(C)C(=O)CC(O)=O)C=C1 QQBQJFKONBDWOS-UHFFFAOYSA-N 0.000 claims description 2
- QYDBMASYHYCYGQ-UHFFFAOYSA-N 5-[4-(2-methylpropyl)phenyl]-1-phenylhexane-2,4-dione Chemical compound C1=CC(CC(C)C)=CC=C1C(C)C(=O)CC(=O)CC1=CC=CC=C1 QYDBMASYHYCYGQ-UHFFFAOYSA-N 0.000 claims description 2
- YAEGTFPZMYVSKV-UHFFFAOYSA-N 5-[4-(2-methylpropyl)phenyl]hexane-2,4-dione Chemical compound CC(C)CC1=CC=C(C(C)C(=O)CC(C)=O)C=C1 YAEGTFPZMYVSKV-UHFFFAOYSA-N 0.000 claims description 2
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 claims description 2
- YRBDAXYIDSJKAT-QGZVFWFLSA-N tert-butyl n-[(6r)-6-[4-(2-methylpropyl)phenyl]-5-oxoheptyl]carbamate Chemical compound CC(C)CC1=CC=C([C@@H](C)C(=O)CCCCNC(=O)OC(C)(C)C)C=C1 YRBDAXYIDSJKAT-QGZVFWFLSA-N 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 8
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 102000004890 Interleukin-8 Human genes 0.000 claims 2
- 108090001007 Interleukin-8 Proteins 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 230000035605 chemotaxis Effects 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 1
- 206010009900 Colitis ulcerative Diseases 0.000 claims 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims 1
- 206010016654 Fibrosis Diseases 0.000 claims 1
- 206010018364 Glomerulonephritis Diseases 0.000 claims 1
- SOWBFZRMHSNYGE-UHFFFAOYSA-N Monoamide-Oxalic acid Natural products NC(=O)C(O)=O SOWBFZRMHSNYGE-UHFFFAOYSA-N 0.000 claims 1
- 206010034277 Pemphigoid Diseases 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 208000000594 bullous pemphigoid Diseases 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 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 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 230000004761 fibrosis Effects 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 208000028867 ischemia Diseases 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims 1
- 230000010410 reperfusion Effects 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP02027453.6 | 2002-12-10 | ||
| EP02027453 | 2002-12-10 | ||
| PCT/EP2003/013946 WO2004052830A1 (en) | 2002-12-10 | 2003-12-09 | Chiral arylketones in the treatement of neutrophil-dependent inflammatory deseases |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2006509022A JP2006509022A (ja) | 2006-03-16 |
| JP2006509022A5 true JP2006509022A5 (enExample) | 2007-03-01 |
| JP5021169B2 JP5021169B2 (ja) | 2012-09-05 |
Family
ID=32479711
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004558041A Expired - Fee Related JP5021169B2 (ja) | 2002-12-10 | 2003-12-09 | 好中球依存性炎症性疾患の治療におけるキラルアリールケトン |
Country Status (16)
| Country | Link |
|---|---|
| US (2) | US20060247297A1 (enExample) |
| EP (1) | EP1581474B1 (enExample) |
| JP (1) | JP5021169B2 (enExample) |
| CN (1) | CN100383110C (enExample) |
| AT (1) | ATE406343T1 (enExample) |
| AU (1) | AU2003289993B8 (enExample) |
| CA (1) | CA2507765C (enExample) |
| CY (1) | CY1108596T1 (enExample) |
| DE (1) | DE60323264D1 (enExample) |
| DK (1) | DK1581474T3 (enExample) |
| ES (1) | ES2312834T3 (enExample) |
| NO (1) | NO332223B1 (enExample) |
| PT (1) | PT1581474E (enExample) |
| RU (1) | RU2345759C2 (enExample) |
| SI (1) | SI1581474T1 (enExample) |
| WO (1) | WO2004052830A1 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2421213C1 (ru) * | 2010-02-24 | 2011-06-20 | Новосибирский институт органической химии им. Н.Н. Ворожцова Сибирского отделения Российской академии наук (НИОХ СО РАН) | Применение 2-гидрокси-3-метил-6-(1-метилэтенил)циклогекс-3-енона в качестве анальгезирующего средства |
| CN109928868A (zh) * | 2019-03-22 | 2019-06-25 | 河北科技大学 | 1,3-双(2,5-二甲基苯基)丙-2-酮的合成方法及其应用 |
| CN115894198B (zh) * | 2022-11-04 | 2024-05-17 | 浙江永太科技股份有限公司 | Qulipta的关键中间体1-(2,3,6-三氟苯基)丙烷-2-酮的制备方法 |
| KR102597093B1 (ko) * | 2023-06-07 | 2023-11-03 | 옙바이오 주식회사 | 줄기세포 노화 억제 신규 화합물 및 이의 약학적 용도 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL267502A (enExample) * | 1960-07-26 | |||
| US3591350A (en) * | 1968-06-17 | 1971-07-06 | M & T Chemicals Inc | Novel plating process |
| SE385883B (sv) * | 1972-04-10 | 1976-07-26 | Ciba Geigy Ag | Forfarande for framstellning av nya pyridinkarbonsyraestrar |
| JPS5842851B2 (ja) | 1976-03-05 | 1983-09-22 | 三井東圧化学株式会社 | ２−（４′−アルキルフエニル）プロピオン酸の製造方法 |
| US4151172A (en) | 1977-08-11 | 1979-04-24 | E. R. Squibb & Sons, Inc. | Phosphonoacyl prolines and related compounds |
| JPS5697249A (en) | 1979-12-30 | 1981-08-05 | Ota Seiyaku Kk | Preparation of 2-arylalkane acid |
| JP2782359B2 (ja) | 1989-06-22 | 1998-07-30 | 日本石油化学株式会社 | ２―（４―イソブチルフエニル）―２―ブテン |
| AU644281B2 (en) | 1991-04-24 | 1993-12-02 | Sumitomo Pharmaceuticals Company, Limited | Novel thiazole derivatives |
| JPH05286902A (ja) * | 1992-04-10 | 1993-11-02 | Sumitomo Pharmaceut Co Ltd | α−クロロ−β−ケトエステル誘導体の製造方法 |
| IT1303249B1 (it) * | 1998-10-23 | 2000-11-06 | Dompe Spa | Alcune n-(2-aril-propionil)-solfonammidi e preparazionifarmaceutiche che le contengono. |
| IT1317826B1 (it) * | 2000-02-11 | 2003-07-15 | Dompe Spa | Ammidi, utili nell'inibizione della chemiotassi dei neutrofiliindotta da il-8. |
-
2003
- 2003-12-09 DE DE60323264T patent/DE60323264D1/de not_active Expired - Lifetime
- 2003-12-09 PT PT03782344T patent/PT1581474E/pt unknown
- 2003-12-09 AT AT03782344T patent/ATE406343T1/de active
- 2003-12-09 WO PCT/EP2003/013946 patent/WO2004052830A1/en not_active Ceased
- 2003-12-09 EP EP03782344A patent/EP1581474B1/en not_active Expired - Lifetime
- 2003-12-09 DK DK03782344T patent/DK1581474T3/da active
- 2003-12-09 US US10/537,824 patent/US20060247297A1/en not_active Abandoned
- 2003-12-09 CA CA2507765A patent/CA2507765C/en not_active Expired - Fee Related
- 2003-12-09 RU RU2005121554/04A patent/RU2345759C2/ru not_active IP Right Cessation
- 2003-12-09 AU AU2003289993A patent/AU2003289993B8/en not_active Ceased
- 2003-12-09 CN CNB200380107685XA patent/CN100383110C/zh not_active Expired - Fee Related
- 2003-12-09 ES ES03782344T patent/ES2312834T3/es not_active Expired - Lifetime
- 2003-12-09 SI SI200331435T patent/SI1581474T1/sl unknown
- 2003-12-09 JP JP2004558041A patent/JP5021169B2/ja not_active Expired - Fee Related
-
2005
- 2005-06-23 NO NO20053086A patent/NO332223B1/no not_active IP Right Cessation
-
2008
- 2008-11-26 CY CY20081101364T patent/CY1108596T1/el unknown
- 2008-12-03 US US12/327,767 patent/US9328057B2/en not_active Expired - Fee Related
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