JP2006517560A5 - - Google Patents
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- Publication number
- JP2006517560A5 JP2006517560A5 JP2006501815A JP2006501815A JP2006517560A5 JP 2006517560 A5 JP2006517560 A5 JP 2006517560A5 JP 2006501815 A JP2006501815 A JP 2006501815A JP 2006501815 A JP2006501815 A JP 2006501815A JP 2006517560 A5 JP2006517560 A5 JP 2006517560A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- methyl
- pyran
- group
- methylsulfinyl
- 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.)
- Pending
Links
- 150000001875 compounds Chemical class 0.000 claims 21
- 239000000203 mixture Substances 0.000 claims 10
- 125000000217 alkyl group Chemical group 0.000 claims 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 8
- 125000005843 halogen group Chemical group 0.000 claims 7
- -1 hydroxycarbonyl groups Chemical group 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- 238000000034 method Methods 0.000 claims 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 239000002904 solvent Substances 0.000 claims 3
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims 3
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 2
- XMNWKNFHHSFESN-UHFFFAOYSA-N ClC1=CC(=C(OC2=C(OC(=CC2=O)C)C2=CC=C(C=C2)S(=O)C)C=C1)F.FC1=C(OC2=C(OC(=CC2=O)C)C2=CC=C(C=C2)S(=O)C)C=CC(=C1)F Chemical compound ClC1=CC(=C(OC2=C(OC(=CC2=O)C)C2=CC=C(C=C2)S(=O)C)C=C1)F.FC1=C(OC2=C(OC(=CC2=O)C)C2=CC=C(C=C2)S(=O)C)C=CC(=C1)F XMNWKNFHHSFESN-UHFFFAOYSA-N 0.000 claims 2
- 206010009944 Colon cancer Diseases 0.000 claims 2
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims 2
- 206010061218 Inflammation Diseases 0.000 claims 2
- 241001465754 Metazoa Species 0.000 claims 2
- 208000002193 Pain Diseases 0.000 claims 2
- 206010037660 Pyrexia Diseases 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims 2
- 230000004054 inflammatory process Effects 0.000 claims 2
- 230000002401 inhibitory effect Effects 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000001624 naphthyl group Chemical group 0.000 claims 2
- 230000004770 neurodegeneration Effects 0.000 claims 2
- 208000015122 neurodegenerative disease Diseases 0.000 claims 2
- 239000007800 oxidant agent Substances 0.000 claims 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims 2
- 229940127293 prostanoid Drugs 0.000 claims 2
- 150000003814 prostanoids Chemical class 0.000 claims 2
- 230000016160 smooth muscle contraction Effects 0.000 claims 2
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 125000004434 sulfur atom Chemical group 0.000 claims 2
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims 2
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 claims 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical group ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims 1
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims 1
- UHXBJUHBIWWBPR-UHFFFAOYSA-N 3-(2,4-dibromophenoxy)-6-methyl-2-(4-methylsulfinylphenyl)pyran-4-one Chemical compound BrC1=C(OC2=C(OC(=CC2=O)C)C2=CC=C(C=C2)S(=O)C)C=CC(=C1)Br UHXBJUHBIWWBPR-UHFFFAOYSA-N 0.000 claims 1
- SWTYZBNPBSTVNO-UHFFFAOYSA-N 3-(2-bromophenoxy)-6-methyl-2-(4-methylsulfinylphenyl)pyran-4-one Chemical compound C=1C=C(S(C)=O)C=CC=1C=1OC(C)=CC(=O)C=1OC1=CC=CC=C1Br SWTYZBNPBSTVNO-UHFFFAOYSA-N 0.000 claims 1
- JZYGNSNKBTXZLJ-UHFFFAOYSA-N 3-(2-chloro-4-methylphenoxy)-6-methyl-2-(4-methylsulfinylphenyl)pyran-4-one Chemical compound ClC1=CC(C)=CC=C1OC1=C(C=2C=CC(=CC=2)S(C)=O)OC(C)=CC1=O JZYGNSNKBTXZLJ-UHFFFAOYSA-N 0.000 claims 1
- ZAGZBIZSAODIBG-UHFFFAOYSA-N 3-(2-fluoro-4-methylphenoxy)-6-methyl-2-(4-methylsulfinylphenyl)pyran-4-one Chemical compound FC1=CC(C)=CC=C1OC1=C(C=2C=CC(=CC=2)S(C)=O)OC(C)=CC1=O ZAGZBIZSAODIBG-UHFFFAOYSA-N 0.000 claims 1
- LRGCMGSFOVPALE-UHFFFAOYSA-N 3-(3-bromophenoxy)-6-methyl-2-(4-methylsulfinylphenyl)pyran-4-one Chemical compound BrC=1C=C(OC2=C(OC(=CC2=O)C)C2=CC=C(C=C2)S(=O)C)C=CC=1 LRGCMGSFOVPALE-UHFFFAOYSA-N 0.000 claims 1
- OVKKZRXNHVYQKY-UHFFFAOYSA-N 3-(4-bromo-2-chlorophenoxy)-6-methyl-2-(4-methylsulfinylphenyl)pyran-4-one Chemical compound BrC1=CC(=C(OC2=C(OC(=CC2=O)C)C2=CC=C(C=C2)S(=O)C)C=C1)Cl OVKKZRXNHVYQKY-UHFFFAOYSA-N 0.000 claims 1
- RZDNFEBTJXOTQW-UHFFFAOYSA-N 3-(4-bromo-2-fluorophenoxy)-6-methyl-2-(4-methylsulfinylphenyl)pyran-4-one Chemical compound C=1C=C(S(C)=O)C=CC=1C=1OC(C)=CC(=O)C=1OC1=CC=C(Br)C=C1F RZDNFEBTJXOTQW-UHFFFAOYSA-N 0.000 claims 1
- HHKBCGKZRATJJS-UHFFFAOYSA-N 3-(4-chloro-2-methylphenoxy)-6-methyl-2-(4-methylsulfinylphenyl)pyran-4-one Chemical compound ClC1=CC(=C(OC2=C(OC(=CC2=O)C)C2=CC=C(C=C2)S(=O)C)C=C1)C HHKBCGKZRATJJS-UHFFFAOYSA-N 0.000 claims 1
- XXDKQLSSQGPHCS-UHFFFAOYSA-N 3-(4-fluoro-2-methylphenoxy)-6-methyl-2-(4-methylsulfinylphenyl)pyran-4-one Chemical compound FC1=CC(=C(OC2=C(OC(=CC2=O)C)C2=CC=C(C=C2)S(=O)C)C=C1)C XXDKQLSSQGPHCS-UHFFFAOYSA-N 0.000 claims 1
- ZCCLJVFGLVAYFA-UHFFFAOYSA-N 6-methyl-3-(2-methylphenoxy)-2-(4-methylsulfinylphenyl)pyran-4-one Chemical compound CS(=O)C1=CC=C(C=C1)C=1OC(=CC(C=1OC1=C(C=CC=C1)C)=O)C ZCCLJVFGLVAYFA-UHFFFAOYSA-N 0.000 claims 1
- ZLWHNMIJIHYPKX-UHFFFAOYSA-N 6-methyl-3-(3-methylphenoxy)-2-(4-methylsulfinylphenyl)pyran-4-one Chemical compound CS(=O)C1=CC=C(C=C1)C=1OC(=CC(C=1OC1=CC(=CC=C1)C)=O)C ZLWHNMIJIHYPKX-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- CVQUWLDCFXOXEN-UHFFFAOYSA-N Pyran-4-one Chemical compound O=C1C=COC=C1 CVQUWLDCFXOXEN-UHFFFAOYSA-N 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 125000004663 dialkyl amino group Chemical group 0.000 claims 1
- YSAVZVORKRDODB-WDSKDSINSA-N diethyl tartrate Chemical compound CCOC(=O)[C@@H](O)[C@H](O)C(=O)OCC YSAVZVORKRDODB-WDSKDSINSA-N 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 1
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES200300355A ES2213485B1 (es) | 2003-02-13 | 2003-02-13 | Derivados de la 2-fenilpiran-4-ona. |
| PCT/EP2004/001295 WO2004072058A1 (en) | 2003-02-13 | 2004-02-12 | 2-phenylpyran-4-one derivatives as selective cox-2 inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2006517560A JP2006517560A (ja) | 2006-07-27 |
| JP2006517560A5 true JP2006517560A5 (https=) | 2007-03-08 |
Family
ID=32865136
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006501815A Pending JP2006517560A (ja) | 2003-02-13 | 2004-02-12 | 選択的ｃｏｘ−２阻害剤としての２−フェニルピラン−４−オン誘導体 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US7582676B2 (https=) |
| EP (1) | EP1592680B9 (https=) |
| JP (1) | JP2006517560A (https=) |
| CN (1) | CN100436438C (https=) |
| AT (1) | ATE394386T1 (https=) |
| DE (1) | DE602004013542D1 (https=) |
| ES (2) | ES2213485B1 (https=) |
| WO (1) | WO2004072058A1 (https=) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2213485B1 (es) | 2003-02-13 | 2005-12-16 | Almirall Prodesfarma, S.A. | Derivados de la 2-fenilpiran-4-ona. |
| ES2214130B1 (es) * | 2003-02-13 | 2005-12-01 | Almirall Prodesfarma, S.A. | 2-3'-bipiridinas. |
| ES2214129B1 (es) * | 2003-02-13 | 2005-12-01 | Almirall Prodesfarma, S.A. | 3-fenilfuran-2-onas. |
Family Cites Families (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4304728A (en) * | 1979-04-05 | 1981-12-08 | Lilly Industries Limited | 6-Substituted pyranone compounds and their use as pharmaceuticals |
| US6486194B2 (en) | 1993-06-24 | 2002-11-26 | Merck Frosst Canada, Inc. | Use of inhibitors of cyclooxygenase in the treatment of neurodegenerative diseases |
| US5585504A (en) | 1994-09-16 | 1996-12-17 | Merck & Co., Inc. | Process of making cox-2 inhibitors having a lactone bridge |
| GB2294879A (en) | 1994-10-19 | 1996-05-15 | Merck & Co Inc | Cylcooxygenase-2 Inhibitors |
| US6231888B1 (en) * | 1996-01-18 | 2001-05-15 | Perio Products Ltd. | Local delivery of non steroidal anti inflammatory drugs (NSAIDS) to the colon as a treatment for colonic polyps |
| ES2125161B1 (es) | 1996-03-21 | 1999-11-16 | Grupo Farmaceutico Almirall S | Nuevos derivados de 2-(3h)-oxazolona. |
| CN1140267C (zh) | 1996-05-17 | 2004-03-03 | 麦克公司 | 治疗环加氧酶-2介导的疾病的每天一次的组合物 |
| IL127441A (en) | 1996-07-18 | 2003-02-12 | Merck Frosst Canada Inc | Substituted pyridines, pharmaceutical compositions comprising them and their use in the preparation of anti-inflammatory medicaments or as selective cyclooxygenase-2 inhibitors |
| US6307047B1 (en) * | 1997-08-22 | 2001-10-23 | Abbott Laboratories | Prostaglandin endoperoxide H synthase biosynthesis inhibitors |
| ES2256817T3 (es) * | 1997-09-05 | 2006-07-16 | Glaxo Group Limited | Composiciones farmaceuticas que comprenden derivados de 2,3-diaril-pirazolo(1,5-b)piridazina. |
| ES2131015B1 (es) | 1997-09-12 | 2000-03-01 | Almirall Prodesfarma Sa | Nuevos derivados de 2-(3h)-oxazolona, procedimientos para su preparacion y su empleo en composiciones farmaceuticas. |
| US5994379A (en) * | 1998-02-13 | 1999-11-30 | Merck Frosst Canada, Inc. | Bisaryl COX-2 inhibiting compounds, compositions and methods of use |
| KR100295206B1 (ko) * | 1998-08-22 | 2001-07-12 | 서경배 | 디아릴벤조피란유도체및이를함유하는시클로옥시게네이즈-2저해제조성물 |
| WO2000014083A1 (en) * | 1998-09-09 | 2000-03-16 | Inflazyme Pharmaceuticals Ltd. | SUBSTITUTED η-PHENYL-Δ-LACTONES AND ANALOGS THEREOF AND USES RELATED THERETO |
| TW587079B (en) * | 1998-09-25 | 2004-05-11 | Almirall Prodesfarma Ag | 2-phenylpyran-4-one derivatives |
| ES2154561B1 (es) * | 1998-09-25 | 2001-12-01 | Almirall Prodesfarma Sa | Derivados de 2-fenilpiran-4-ona. |
| US6303972B1 (en) * | 1998-11-25 | 2001-10-16 | Micron Technology, Inc. | Device including a conductive layer protected against oxidation |
| DZ3265A1 (fr) | 1999-04-14 | 2000-10-19 | Pacific Corp | Derives de 4,5-diaryl-3(2h)-furanone comme inhibiteurs de cyclo-oxygenase-2 |
| AU5873000A (en) | 1999-06-24 | 2001-01-31 | Pharmacia Corporation | Combination of tumors necrocis factor (tnf) antagonists and cox-2 inhibitors forthe treatment of inflammation |
| DE60006057T2 (de) * | 1999-12-03 | 2004-05-27 | Pfizer Products Inc., Groton | Heteroarylphenylpyrazolverbindungen zur Verwendung als analgetisches/entzündungshemmendes Mittel |
| PE20011333A1 (es) * | 2000-03-16 | 2002-01-16 | Almirall Prodesfarma Ag | Derivados de 2-fenilpiran-4-ona como inhibidores de ciclooxigenasa 2 |
| CA2412651A1 (en) * | 2000-05-22 | 2001-11-29 | Dr. Reddy's Laboratories Limited | Novel compounds having antiinflammatory activity: process for their preparation and pharmaceutical compositions containing them |
| WO2001091856A2 (en) | 2000-06-01 | 2001-12-06 | Pharmacia Corporation | Use of cox2 inhibitors for treating skin injury from exposure to ultraviolet radiation |
| JP2004505060A (ja) | 2000-07-27 | 2004-02-19 | ファルマシア・コーポレーション | 炎症関連心臓血管障害を防止するかまたは治療するためのアルドステロンアンタゴニストおよびシクロオキシゲナーゼ−２阻害剤併用療法 |
| WO2002055502A1 (en) | 2001-01-02 | 2002-07-18 | Fujisawa Pharmaceutical Co., Ltd. | Pyridine derivatives useful as cyclooxygenase inhibitor |
| WO2003006451A1 (en) | 2001-07-10 | 2003-01-23 | Almirall Prodesfarma S.A. | 4-phenylpyran-2-one derivatives |
| EP1492773B1 (en) | 2002-04-05 | 2009-02-04 | Cadila Healthcare Ltd. | 4-(heterocyclyl)-benzenesulfoximine compounds for the treatment of inflammation |
| ES2214129B1 (es) | 2003-02-13 | 2005-12-01 | Almirall Prodesfarma, S.A. | 3-fenilfuran-2-onas. |
| ES2214130B1 (es) | 2003-02-13 | 2005-12-01 | Almirall Prodesfarma, S.A. | 2-3'-bipiridinas. |
| ES2213485B1 (es) | 2003-02-13 | 2005-12-16 | Almirall Prodesfarma, S.A. | Derivados de la 2-fenilpiran-4-ona. |
-
2003
- 2003-02-13 ES ES200300355A patent/ES2213485B1/es not_active Expired - Fee Related
-
2004
- 2004-02-12 WO PCT/EP2004/001295 patent/WO2004072058A1/en not_active Ceased
- 2004-02-12 JP JP2006501815A patent/JP2006517560A/ja active Pending
- 2004-02-12 ES ES04710358T patent/ES2303938T4/es not_active Expired - Lifetime
- 2004-02-12 CN CNB2004800087372A patent/CN100436438C/zh not_active Expired - Fee Related
- 2004-02-12 AT AT04710358T patent/ATE394386T1/de not_active IP Right Cessation
- 2004-02-12 DE DE602004013542T patent/DE602004013542D1/de not_active Expired - Fee Related
- 2004-02-12 US US10/544,361 patent/US7582676B2/en not_active Expired - Fee Related
- 2004-02-12 EP EP04710358A patent/EP1592680B9/en not_active Expired - Lifetime
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