HUP9902443A2 - Új eljárás fenilcsoporttal helyettesített 2(5H)-furanon származékok előállítására, intermedierek - Google Patents
Új eljárás fenilcsoporttal helyettesített 2(5H)-furanon származékok előállítására, intermedierekInfo
- Publication number
- HUP9902443A2 HUP9902443A2 HU9902443A HUP9902443A HUP9902443A2 HU P9902443 A2 HUP9902443 A2 HU P9902443A2 HU 9902443 A HU9902443 A HU 9902443A HU P9902443 A HUP9902443 A HU P9902443A HU P9902443 A2 HUP9902443 A2 HU P9902443A2
- Authority
- HU
- Hungary
- Prior art keywords
- solvent
- formula
- resulting compound
- reacted
- intermediates
- Prior art date
Links
- 239000000543 intermediate Substances 0.000 title abstract 2
- 238000000034 method Methods 0.000 title abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 7
- 239000002904 solvent Substances 0.000 abstract 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- DGMOBVGABMBZSB-UHFFFAOYSA-N 2-methylpropanoyl chloride Chemical compound CC(C)C(Cl)=O DGMOBVGABMBZSB-UHFFFAOYSA-N 0.000 abstract 1
- 102000010907 Cyclooxygenase 2 Human genes 0.000 abstract 1
- 108010037462 Cyclooxygenase 2 Proteins 0.000 abstract 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 1
- 239000002841 Lewis acid Substances 0.000 abstract 1
- 239000000010 aprotic solvent Substances 0.000 abstract 1
- 239000011230 binding agent Substances 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 229910052801 chlorine Chemical group 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 230000018044 dehydration Effects 0.000 abstract 1
- 238000006297 dehydration reaction Methods 0.000 abstract 1
- 201000010099 disease Diseases 0.000 abstract 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 1
- 229910052731 fluorine Inorganic materials 0.000 abstract 1
- 239000011737 fluorine Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 150000007517 lewis acids Chemical class 0.000 abstract 1
- 230000001404 mediated effect Effects 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- 239000007800 oxidant agent Substances 0.000 abstract 1
- HNKJADCVZUBCPG-UHFFFAOYSA-N thioanisole Chemical compound CSC1=CC=CC=C1 HNKJADCVZUBCPG-UHFFFAOYSA-N 0.000 abstract 1
- -1 tri-substituted phenyl Chemical group 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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
- C07D307/56—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/60—Two oxygen atoms, e.g. succinic anhydride
-
- 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
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/32—Oxygen atoms
- C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C315/00—Preparation of sulfones; Preparation of sulfoxides
- C07C315/02—Preparation of sulfones; Preparation of sulfoxides by formation of sulfone or sulfoxide groups by oxidation of sulfides, or by formation of sulfone groups by oxidation of sulfoxides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/24—Sulfones; Sulfoxides having sulfone or sulfoxide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
- C07C319/20—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides by reactions not involving the formation of sulfide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/125—Saturated compounds having only one carboxyl group and containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/48—Compounds containing oxirane rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms, e.g. ester or nitrile radicals
-
- 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
- C07D307/56—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/58—One oxygen atom, e.g. butenolide
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Fertilizers (AREA)
- Furan Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
A találmány tárgya a ciklooxigenáz-2 által közvetített betegségekellen hatásos (I) és (Ia) általános képletű vegyületek - ahol aképletben R' jelentése (a) egyenes vagy elágazó láncú 1-6 szénatomos alkilcsoport; (b) mono-, di- vagy triszubsztituált fenil- vagy naftilcsoport, X jelentése hidrogén, fluor- vagy klóratom - előállítására szolgálóeljárás. Az eljárás során (a) tioanizolt nem reakcióképes oldószer ésvalamely Lewis-sav jelenlétében izobutiril-kloriddal reagáltatnak, (b)majd a kapott vegyületet brómozószerrel nem reakcióképes oldószerbenegy második oldószer, például etil-acetát jelenlétében brómozzák, (c)majd a kapott vegyületet nem reakcióképes oldószerben oxidálószerrel,adott esetben megfelelő katalizátor alkalmazásával oxidálják, (d) majda kapott vegyületet alkanol oldószerben egy R'OCH2COOH képletűvegyülettel reagáltatják megfelelő bázis jelenlétében, majd (e) akapott vegyületet aprotikus oldószerben erős bázissal reagáltatják, ésaz így kapott ciklizált termékből vízmegkötő szer jelenlétében történődehidratálással nyerik az (I) általános képletű vegyületeket. Atalálmány tárgyát képezik még (A) általános képletű intermedierek is,ahol a képletben R jelentése 1-6 szénatomos alkilcsoport. Ó
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US1864496P | 1996-05-31 | 1996-05-31 | |
| GBGB9613110.7A GB9613110D0 (en) | 1996-06-21 | 1996-06-21 | Process for making phenyl heterocyclic useful as cox-2 inhibitors |
| US2810896P | 1996-10-09 | 1996-10-09 | |
| US2810996P | 1996-10-09 | 1996-10-09 | |
| GBGB9622831.7A GB9622831D0 (en) | 1996-11-01 | 1996-11-01 | Process for making phenyl heterocycles useful as cox-2 inhibitors |
| GBGB9622816.8A GB9622816D0 (en) | 1996-11-01 | 1996-11-01 | Process for making phenyl heterocycles useful as cox-2 inhibitors |
| PCT/US1997/009193 WO1997045420A1 (en) | 1996-05-31 | 1997-05-27 | Process for making phenyl heterocycles useful as cox-2 inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HUP9902443A2 true HUP9902443A2 (hu) | 2001-04-28 |
| HUP9902443A3 HUP9902443A3 (en) | 2001-05-28 |
Family
ID=27547262
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU9902443A HUP9902443A3 (en) | 1996-05-31 | 1997-05-27 | New process for making phenyl substituted 2(5h)-furanones, intermediates |
Country Status (19)
| Country | Link |
|---|---|
| EP (1) | EP0906300B1 (hu) |
| JP (1) | JP3149192B2 (hu) |
| KR (1) | KR20000016043A (hu) |
| CN (1) | CN1219931A (hu) |
| AT (1) | ATE212019T1 (hu) |
| AU (1) | AU713380B2 (hu) |
| BR (1) | BR9709264A (hu) |
| CA (1) | CA2255635A1 (hu) |
| CZ (1) | CZ391498A3 (hu) |
| DE (1) | DE69709639T2 (hu) |
| EA (1) | EA199801084A1 (hu) |
| ES (1) | ES2169399T3 (hu) |
| HR (1) | HRP970289A2 (hu) |
| HU (1) | HUP9902443A3 (hu) |
| NZ (1) | NZ332637A (hu) |
| PL (1) | PL330227A1 (hu) |
| SK (1) | SK164698A3 (hu) |
| WO (1) | WO1997045420A1 (hu) |
| YU (1) | YU53998A (hu) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2201466T3 (es) * | 1997-03-14 | 2004-03-16 | MERCK FROSST CANADA & CO. | `(metilsulfonil)fenil-2-(5h)-furanonas con enlace con oxigeno como inhibidores de cox-2`. |
| US6071954A (en) * | 1997-03-14 | 2000-06-06 | Merk Frosst Canada, Inc. | (methylsulfonyl)phenyl-2-(5H)-furanones with oxygen link as COX-2 inhibitors |
| GB2330833A (en) * | 1997-10-29 | 1999-05-05 | Merck & Co Inc | PREPARATION OF 4-(4-Methylsulfonylphenyl)-2-furanones USEFUL AS COX-2 INHIBITORS |
| JP2002506024A (ja) * | 1998-03-13 | 2002-02-26 | メルク エンド カムパニー インコーポレーテッド | 急性冠動脈虚血症候群および関連状態に対する併用療法および組成物 |
| FR2799462B1 (fr) * | 1999-10-08 | 2004-05-28 | Merial Sas | Procede de preparation d'inhibiteurs cox-2 |
| PL1745791T3 (pl) | 2003-05-07 | 2013-11-29 | Osteologix As | Leczenie chorób chrząstki/kości za pomocą rozpuszczalnych w wodzie soli strontu |
| JP6204583B2 (ja) | 2014-05-15 | 2017-09-27 | 富士フイルム株式会社 | α−ブロモアセトフェノン化合物の製造方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0759432A1 (en) * | 1993-01-15 | 1997-02-26 | G.D. Searle & Co. | Use of medicaments containing 3,4-diaryl furans and analogs thereof for treating a skin-related condition |
| WO1994026731A1 (en) * | 1993-05-13 | 1994-11-24 | Merck Frosst Canada Inc. | 2-substituted-3,4-diarylthiophene derivatives as inhibitors of cyclooxygenase |
| US5474995A (en) * | 1993-06-24 | 1995-12-12 | Merck Frosst Canada, Inc. | Phenyl heterocycles as cox-2 inhibitors |
| US5585504A (en) * | 1994-09-16 | 1996-12-17 | Merck & Co., Inc. | Process of making cox-2 inhibitors having a lactone bridge |
| AU702591B2 (en) * | 1994-12-21 | 1999-02-25 | Merck Frosst Canada Ltd. | Diaryl-2-(5H)-furanones as cox-2 inhibitors |
-
1997
- 1997-05-26 HR HR9622816.8A patent/HRP970289A2/xx not_active Application Discontinuation
- 1997-05-27 DE DE69709639T patent/DE69709639T2/de not_active Expired - Fee Related
- 1997-05-27 EA EA199801084A patent/EA199801084A1/ru unknown
- 1997-05-27 EP EP97927840A patent/EP0906300B1/en not_active Expired - Lifetime
- 1997-05-27 AU AU32203/97A patent/AU713380B2/en not_active Ceased
- 1997-05-27 ES ES97927840T patent/ES2169399T3/es not_active Expired - Lifetime
- 1997-05-27 AT AT97927840T patent/ATE212019T1/de not_active IP Right Cessation
- 1997-05-27 JP JP54295397A patent/JP3149192B2/ja not_active Expired - Fee Related
- 1997-05-27 PL PL97330227A patent/PL330227A1/xx unknown
- 1997-05-27 NZ NZ332637A patent/NZ332637A/en unknown
- 1997-05-27 CN CN97194963A patent/CN1219931A/zh active Pending
- 1997-05-27 BR BR9709264A patent/BR9709264A/pt unknown
- 1997-05-27 CA CA002255635A patent/CA2255635A1/en not_active Abandoned
- 1997-05-27 CZ CZ983914A patent/CZ391498A3/cs unknown
- 1997-05-27 SK SK1646-98A patent/SK164698A3/sk unknown
- 1997-05-27 KR KR1019980709608A patent/KR20000016043A/ko not_active Application Discontinuation
- 1997-05-27 WO PCT/US1997/009193 patent/WO1997045420A1/en not_active Application Discontinuation
- 1997-05-27 HU HU9902443A patent/HUP9902443A3/hu unknown
-
1998
- 1998-11-27 YU YU53998A patent/YU53998A/sr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JP3149192B2 (ja) | 2001-03-26 |
| AU713380B2 (en) | 1999-12-02 |
| JPH11511753A (ja) | 1999-10-12 |
| PL330227A1 (en) | 1999-05-10 |
| SK164698A3 (en) | 1999-07-12 |
| DE69709639T2 (de) | 2002-08-08 |
| EP0906300B1 (en) | 2002-01-16 |
| DE69709639D1 (de) | 2002-02-21 |
| ES2169399T3 (es) | 2002-07-01 |
| YU53998A (en) | 1999-11-22 |
| CA2255635A1 (en) | 1997-12-04 |
| HRP970289A2 (en) | 1998-04-30 |
| EA199801084A1 (ru) | 1999-04-29 |
| CZ391498A3 (cs) | 1999-04-14 |
| BR9709264A (pt) | 1999-08-10 |
| NZ332637A (en) | 2000-06-23 |
| ATE212019T1 (de) | 2002-02-15 |
| WO1997045420A1 (en) | 1997-12-04 |
| HUP9902443A3 (en) | 2001-05-28 |
| EP0906300A1 (en) | 1999-04-07 |
| AU3220397A (en) | 1998-01-05 |
| CN1219931A (zh) | 1999-06-16 |
| KR20000016043A (ko) | 2000-03-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| FI971312A (fi) | Uudet prostaglandiinisyntaasin estäjät | |
| ATE367371T1 (de) | Verfahren zur herstellung von fluorverbindungen mittels flüssigphasenfluorierung | |
| HUP9902443A2 (hu) | Új eljárás fenilcsoporttal helyettesített 2(5H)-furanon származékok előállítására, intermedierek | |
| RU98111204A (ru) | Способы и промежуточные продукты для получения 1-бензил-4-((5,6-диметокси-1- инданон)-2-ил)-метилпиперидина | |
| DE69524103D1 (de) | Fluorinierte 2-nitroimidazole analoge zur detektion von hypoxischen tumorzellen | |
| ES2186297T3 (es) | Procedimiento para la preparacion de derivados de imidazoquinazolinona. | |
| DK0610138T3 (da) | Fremgangsmåde til fremstilling af 6 alpha,9 alpha-difluorsteroider samt mellemprodukter dertil | |
| SE7605819L (sv) | Nya propargyl-2-fenylaminoimidazolin-(2), dess syraadditionssalter, lekemedel innehallande dessa och forfarande for framstellning derav | |
| EA200100894A1 (ru) | Новый способ получения алендроновой кислоты | |
| DK1392672T3 (da) | Chlormethylering af thiopen | |
| JPS5777671A (en) | Preparation of hydroxyindoles ( or 1,4-dihydroisoquinolones) and their intermediate | |
| KR960029345A (ko) | 트리플루오로메틸-치환된 2-아자비시클로옥탄을 함유하는 신규 아실화 슈도펩티드 | |
| EP0194064A3 (en) | Azolyl substituted aralkyl compounds | |
| JPS55108898A (en) | 25-hydroxy-24-oxocholesterol derivative and its preparation | |
| ATE157655T1 (de) | Verfahren zur herstellung von gegebenfalls 2- substituierten 5-chlorimidazolen | |
| ATE142637T1 (de) | Neues verfahren zur herstellung von 20-oxo, 17- alpha, 21-dihydroxy derivaten von pregnan und neue zwischenprodukte dafür | |
| DE59010041D1 (de) | Herstellung von Dioxolanderivaten | |
| KR880009031A (ko) | 티아졸로벤즈이미다졸의 제조방법 및 그의 중간체 | |
| JPS60158137A (ja) | 含フツ素アクリル酸誘導体の製法 | |
| JPS55108838A (en) | Preparation of arkyl-1-chloro-2-oxocycloalkane carboxylate | |
| JPS56113745A (en) | Preparation of bromonitroalcohol | |
| JPS56136984A (en) | Production of parachloroalkoxy benzene | |
| JPS5231089A (en) | Preparation of 3-acyloxy-3- methylcephalosporins derivatives | |
| JPS577439A (en) | Production of levulinic acid or its ester | |
| DK0609254T3 (da) | Fremgangsmåde til fremstilling af 2,5-dihydroxyphenyleddikesyre |