AR007695A1 - Procedimiento para preparar fenilheterociclos utiles como inhibidores de cox-2 - Google Patents
Procedimiento para preparar fenilheterociclos utiles como inhibidores de cox-2Info
- Publication number
- AR007695A1 AR007695A1 ARP970102940A ARP970102940A AR007695A1 AR 007695 A1 AR007695 A1 AR 007695A1 AR P970102940 A ARP970102940 A AR P970102940A AR P970102940 A ARP970102940 A AR P970102940A AR 007695 A1 AR007695 A1 AR 007695A1
- Authority
- AR
- Argentina
- Prior art keywords
- formula
- compound
- reacting
- give
- cox
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 title 1
- 229940111134 coxibs Drugs 0.000 title 1
- 239000003255 cyclooxygenase 2 inhibitor Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 3
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 2
- 239000012442 inert solvent Substances 0.000 abstract 2
- SHAHPWSYJFYMRX-GDLCADMTSA-N (2S)-2-(4-{[(1R,2S)-2-hydroxycyclopentyl]methyl}phenyl)propanoic acid Chemical compound C1=CC([C@@H](C(O)=O)C)=CC=C1C[C@@H]1[C@@H](O)CCC1 SHAHPWSYJFYMRX-GDLCADMTSA-N 0.000 abstract 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- 102000010907 Cyclooxygenase 2 Human genes 0.000 abstract 1
- 108010037462 Cyclooxygenase 2 Proteins 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 206010061218 Inflammation Diseases 0.000 abstract 1
- 150000001242 acetic acid derivatives Chemical class 0.000 abstract 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 abstract 1
- 239000012346 acetyl chloride Substances 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 201000010099 disease Diseases 0.000 abstract 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 230000004054 inflammatory process Effects 0.000 abstract 1
- 150000007529 inorganic bases Chemical class 0.000 abstract 1
- 230000001404 mediated effect Effects 0.000 abstract 1
- 150000007530 organic bases Chemical class 0.000 abstract 1
- 125000000962 organic group Chemical group 0.000 abstract 1
- 239000007800 oxidant agent Substances 0.000 abstract 1
- 239000003444 phase transfer catalyst Substances 0.000 abstract 1
- 239000003880 polar aprotic solvent Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- HNKJADCVZUBCPG-UHFFFAOYSA-N thioanisole Chemical compound CSC1=CC=CC=C1 HNKJADCVZUBCPG-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Un procedimiento para preparar fenilheterociclos de fórmula I útiles en el tratamiento de la inflamación y otras enfermedades mediadas por ciclooxigenasa-2, de fórmula (I) en donde R2 es un grupo orgánico de reacción estable tal como fenilmono -o di-sustituido en donde el sustituyente se selecciona delgrupo que consiste de: (1) hidrógeno, (2) halógeno, (3) alcoxi C1-6 (4) tialquil C1-6, (5) CH, (6) CF3, y (7) alquil C1-6; R3 y R3 se seleccionan cadauno independientemente dehidróge no y alquil C1-4, que comprende: (b) hacer reaccionar tioanisol en un solvente inerte en presencia de cloruro de acetilo ycloruro de aluminio para dar un compuesto de fórmula 3; (b2) hacer reaccionar un compuesto de fórmula 3 en unsolvente ine rte en presencia de un catalizadorde transferencia de fase y un agente oxidante para dar un compuesto de fórmula 4.(b) hacer reaccionar un compuesto de fórmula 4 en ácido acético acuoso conbromo para dar un compuesto de fórmula 2 (b4)haciendo reacc ionar un compuesto de fórmula 2 en N,N-dimetilformamida con un derivado de ácido acético defórmula 6 en presencia de una base inorgánica para producir un compuesto de fórmula 5a, (b5) tratar el compuesto 5a en un solvente polaraprótico con unab ase orgánica para dar un compuesto de fórmula 1.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US2120096P | 1996-07-03 | 1996-07-03 | |
| GBGB9615867.0A GB9615867D0 (en) | 1996-07-03 | 1996-07-29 | Process of preparing phenyl heterocycles useful as cox-2 inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR007695A1 true AR007695A1 (es) | 1999-11-10 |
Family
ID=26309770
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP970102940A AR007695A1 (es) | 1996-07-03 | 1997-07-01 | Procedimiento para preparar fenilheterociclos utiles como inhibidores de cox-2 |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US5840924A (es) |
| EP (1) | EP0912537B1 (es) |
| JP (1) | JP3071472B2 (es) |
| CN (1) | CN1097046C (es) |
| AR (1) | AR007695A1 (es) |
| AT (1) | ATE266651T1 (es) |
| AU (1) | AU717835B2 (es) |
| BR (1) | BR9710099A (es) |
| CA (1) | CA2258048C (es) |
| CZ (1) | CZ297257B6 (es) |
| DE (1) | DE69729096T2 (es) |
| DK (1) | DK0912537T3 (es) |
| EA (1) | EA001629B1 (es) |
| ES (1) | ES2218691T3 (es) |
| GB (1) | GB9615867D0 (es) |
| HR (1) | HRP970351B1 (es) |
| HU (1) | HU224840B1 (es) |
| NZ (1) | NZ333379A (es) |
| PL (1) | PL195025B1 (es) |
| PT (1) | PT912537E (es) |
| RS (1) | RS49591B (es) |
| SK (1) | SK283997B6 (es) |
| TW (1) | TW419474B (es) |
| UA (1) | UA57029C2 (es) |
| WO (1) | WO1998000416A1 (es) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040072889A1 (en) * | 1997-04-21 | 2004-04-15 | Pharmacia Corporation | Method of using a COX-2 inhibitor and an alkylating-type antineoplastic agent as a combination therapy in the treatment of neoplasia |
| CA2322824A1 (en) * | 1998-03-13 | 1999-09-16 | Merck & Co., Inc. | Combination therapy and composition for acute coronary ischemic syndrome and related conditions |
| US6031108A (en) * | 1998-09-16 | 2000-02-29 | Bayer Corporation | Process for the preparation of 2-(methylsulfonyl)-5-(trifluoromethyl)-1,3,4-thiadiazole (TDA sulfone) |
| US6649645B1 (en) | 1998-12-23 | 2003-11-18 | Pharmacia Corporation | Combination therapy of radiation and a COX-2 inhibitor for treatment of neoplasia |
| AU2001258677A1 (en) * | 2000-05-22 | 2001-12-03 | Dr. Reddy's Research Foundation | Novel compounds having antiinflammatory activity: process for their preparation and pharmaceutical compositions containing them |
| DE10129320A1 (de) * | 2001-06-19 | 2003-04-10 | Norbert Mueller | Verwendung von COX-2 Inhibitoren zur Behandlung von Schizophrenie, wahnhaften Störungen, affektiven Störungen oder Ticstörungen |
| US20060167074A1 (en) * | 2001-06-19 | 2006-07-27 | Norbert Muller | Methods and compositions for the treatment of psychiatric disorders |
| WO2003030812A2 (en) * | 2001-10-10 | 2003-04-17 | Shasun Chemicals And Drugs Limited | 1-[(4-methyl thio)phenyl]-2-(phenyl acetoxy)-1-ethanone and a process for preparing the same |
| WO2003059347A1 (en) * | 2002-01-10 | 2003-07-24 | Pharmacia & Upjohn Company | Use of cox-2 inhibitors in combination with antiviral agents for the treatment of papilloma virus infections |
| TW200403072A (en) * | 2002-01-23 | 2004-03-01 | Upjohn Co | Combination therapy for the treatment of bacterial infections |
| US20040147581A1 (en) * | 2002-11-18 | 2004-07-29 | Pharmacia Corporation | Method of using a Cox-2 inhibitor and a 5-HT1A receptor modulator as a combination therapy |
| US20040220155A1 (en) * | 2003-03-28 | 2004-11-04 | Pharmacia Corporation | Method of providing a steroid-sparing benefit with a cyclooxygenase-2 inhibitor and compositions therewith |
| WO2004098618A2 (en) * | 2003-05-07 | 2004-11-18 | Osteologix A/S | Strontium combinations for prophylaxis/treatment of cartilage and/or bone conditions |
| ES2275218T3 (es) * | 2003-05-07 | 2007-06-01 | Osteologix A/S | Sales de estroncio hidrosolubles para el tratamiento de afecciones de cartilagos y/o huesos. |
| WO2005009342A2 (en) * | 2003-07-16 | 2005-02-03 | Pharmacia Corporation | Method for the treatment or prevention of dermatological disorders with a cyclooxygenase-2 inhibitor alone and in combination with a dermatological treatment agent and compositions therewith |
| US20050119262A1 (en) * | 2003-08-21 | 2005-06-02 | Pharmacia Corporation | Method for preventing or treating an optic neuropathy with a cox-2 inhibitor and an intraocular pressure reducing agent |
| WO2005023189A2 (en) * | 2003-09-03 | 2005-03-17 | Pharmacia Corporation | Method of cox-2 selective inhibitor and nitric oxide-donating agent |
| EP1784179A4 (en) | 2004-08-24 | 2010-03-31 | Merck Sharp & Dohme | COMBINATION THERAPY FOR THE TREATMENT OF CYCLOOXYGENASE-2-MEDIATED DISEASES OR CONDITIONS IN PATIENTS WITH RISK TO THROMBOTIC CARDIOVASCULAR EVENTS |
| AU2006244393B2 (en) * | 2005-05-05 | 2012-06-21 | Cook Biotech Incorporated | Implantable materials and methods for inhibiting tissue adhesion formation |
| CN104774186A (zh) * | 2015-04-28 | 2015-07-15 | 江苏中旗作物保护股份有限公司 | 农药除草剂异恶唑草酮的合成方法 |
| US11096924B2 (en) | 2016-09-07 | 2021-08-24 | Trustees Of Tufts College | Combination therapies using immuno-dash inhibitors and PGE2 antagonists |
| EP3883562A4 (en) | 2018-11-21 | 2022-08-03 | Tremeau Pharmaceuticals, Inc. | PURIFIED FORMS OF ROFECOXIB AND METHODS OF MAKING AND USING |
| US10945992B1 (en) | 2019-11-13 | 2021-03-16 | Tremeau Pharmaceuticals, Inc. | Dosage forms of rofecoxib and related methods |
| US11161833B1 (en) | 2021-04-09 | 2021-11-02 | Tremeau Pharmaceuticals, Inc. | Deuterated etoricoxib, methods of manufacture, and use thereof |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5916884A (ja) * | 1982-07-19 | 1984-01-28 | Fujisawa Pharmaceut Co Ltd | 新規フラン化合物 |
| US4968817A (en) * | 1984-07-27 | 1990-11-06 | National Distillers And Chemical Corporation | Manufacture of gamma-crotonolactone by carbonylation of glycidol |
| DE3615157A1 (de) * | 1986-05-05 | 1987-11-12 | Schwabe Willmar Gmbh & Co | 5-arylalkyl-4-alkoxy-2(5h)-furanone, zwischenprodukte und verfahren zu ihrer herstellung sowie ihre anwendung als therapeutische wirkstoffe |
| DE3718527A1 (de) * | 1987-06-03 | 1988-12-15 | Basf Ag | Verfahren zur herstellung von 2(5h)-furanonen |
| DE4014420A1 (de) * | 1989-09-23 | 1991-04-04 | Bayer Ag | 5h-furan-2-on-derivate |
| US5207817A (en) * | 1989-09-23 | 1993-05-04 | Bayer Aktiengesellschaft | Herbicidal 5H-furan-2-one derivatives |
| AU7559691A (en) * | 1990-04-17 | 1991-11-11 | Allergan, Inc. | 2(5h)-furanones substituted in the 5 and or in the 4 position, as anti-inflammatory agents |
| US5393150A (en) * | 1991-09-05 | 1995-02-28 | Fort; Chris | Bifurcated keyboard arrangement |
| IT1254558B (it) * | 1992-03-26 | 1995-09-25 | Mini Ricerca Scient Tecnolog | Composti a base di 3,4-diaril-(5h)-furan-2-one ad attivita' fungicida 3 |
| CA2152792C (en) * | 1993-01-15 | 2000-02-15 | Stephen R. Bertenshaw | Novel 3,4-diaryl thiophenes and analogs thereof having use as antiinflammatory agents |
| US5474995A (en) * | 1993-06-24 | 1995-12-12 | Merck Frosst Canada, Inc. | Phenyl heterocycles as cox-2 inhibitors |
| JPH09501920A (ja) * | 1993-08-19 | 1997-02-25 | ワーナー−ランバート・コンパニー | 非ペプチドエンドセリンアンタゴニスト▲ｉ▼ |
| WO1995018799A1 (en) * | 1994-01-10 | 1995-07-13 | Merck Frosst Canada Inc. | Phenyl heterocycles as cox-2 inhibitors |
| US5475995A (en) * | 1994-05-16 | 1995-12-19 | Livingston; George G. | Truck spare tire locking rod |
-
1996
- 1996-07-29 GB GBGB9615867.0A patent/GB9615867D0/en active Pending
-
1997
- 1997-06-16 US US08/876,894 patent/US5840924A/en not_active Expired - Fee Related
- 1997-06-27 CZ CZ0436898A patent/CZ297257B6/cs not_active IP Right Cessation
- 1997-06-27 PL PL97330750A patent/PL195025B1/pl not_active IP Right Cessation
- 1997-06-27 HR HR970351A patent/HRP970351B1/xx not_active IP Right Cessation
- 1997-06-27 CN CN97196133A patent/CN1097046C/zh not_active Expired - Fee Related
- 1997-06-27 UA UA99020607A patent/UA57029C2/uk unknown
- 1997-06-27 WO PCT/US1997/011466 patent/WO1998000416A1/en not_active Ceased
- 1997-06-27 JP JP10504411A patent/JP3071472B2/ja not_active Expired - Fee Related
- 1997-06-27 AU AU35886/97A patent/AU717835B2/en not_active Ceased
- 1997-06-27 HU HU9903836A patent/HU224840B1/hu not_active IP Right Cessation
- 1997-06-27 CA CA002258048A patent/CA2258048C/en not_active Expired - Fee Related
- 1997-06-27 DE DE69729096T patent/DE69729096T2/de not_active Expired - Lifetime
- 1997-06-27 NZ NZ333379A patent/NZ333379A/xx not_active IP Right Cessation
- 1997-06-27 PT PT97932424T patent/PT912537E/pt unknown
- 1997-06-27 SK SK1793-98A patent/SK283997B6/sk not_active IP Right Cessation
- 1997-06-27 RS YUP-592/98A patent/RS49591B/sr unknown
- 1997-06-27 AT AT97932424T patent/ATE266651T1/de active
- 1997-06-27 ES ES97932424T patent/ES2218691T3/es not_active Expired - Lifetime
- 1997-06-27 EP EP97932424A patent/EP0912537B1/en not_active Expired - Lifetime
- 1997-06-27 BR BR9710099A patent/BR9710099A/pt not_active IP Right Cessation
- 1997-06-27 EA EA199900079A patent/EA001629B1/ru not_active IP Right Cessation
- 1997-06-27 DK DK97932424T patent/DK0912537T3/da active
- 1997-06-28 TW TW086109096A patent/TW419474B/zh not_active IP Right Cessation
- 1997-07-01 AR ARP970102940A patent/AR007695A1/es active IP Right Grant
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FG | Grant, registration |