KR930004245A - 신규 중간체 및 s-케토프로펜의 제조에 있어서의 그의 용도 - Google Patents
신규 중간체 및 s-케토프로펜의 제조에 있어서의 그의 용도 Download PDFInfo
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- KR930004245A KR930004245A KR1019920015637A KR920015637A KR930004245A KR 930004245 A KR930004245 A KR 930004245A KR 1019920015637 A KR1019920015637 A KR 1019920015637A KR 920015637 A KR920015637 A KR 920015637A KR 930004245 A KR930004245 A KR 930004245A
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- 239000000543 intermediate Substances 0.000 title 1
- 239000002253 acid Substances 0.000 claims abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 25
- 150000001875 compounds Chemical class 0.000 claims 13
- 125000003545 alkoxy group Chemical group 0.000 claims 10
- 125000000217 alkyl group Chemical group 0.000 claims 8
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 5
- 125000004104 aryloxy group Chemical group 0.000 claims 4
- 238000007796 conventional method Methods 0.000 claims 3
- 150000002431 hydrogen Chemical class 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 2
- DKYWVDODHFEZIM-NSHDSACASA-N dexketoprofen Chemical compound OC(=O)[C@@H](C)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 DKYWVDODHFEZIM-NSHDSACASA-N 0.000 claims 2
- 229960002783 dexketoprofen Drugs 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- LCTONWCANYUPML-UHFFFAOYSA-M Pyruvate Chemical compound CC(=O)C([O-])=O LCTONWCANYUPML-UHFFFAOYSA-M 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 1
- 150000001342 alkaline earth metals Chemical class 0.000 claims 1
- 150000003973 alkyl amines Chemical class 0.000 claims 1
- 239000000010 aprotic solvent Substances 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- -1 benzyloxy, acetyloxy, benzoyloxy Chemical group 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 229910002091 carbon monoxide Inorganic materials 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 150000004696 coordination complex Chemical class 0.000 claims 1
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 238000005984 hydrogenation reaction Methods 0.000 claims 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 239000000178 monomer Substances 0.000 claims 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims 1
- 229910003445 palladium oxide Inorganic materials 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 230000007704 transition Effects 0.000 claims 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 229960000991 ketoprofen Drugs 0.000 abstract 1
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- C07C59/40—Unsaturated compounds
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/84—Unsaturated compounds containing keto groups containing six membered aromatic rings
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- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/32—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen
- C07C1/321—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen the hetero-atom being a non-metal atom
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- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/14—Unsaturated ethers
- C07C43/164—Unsaturated ethers containing six-membered aromatic rings
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- C07C43/14—Unsaturated ethers
- C07C43/17—Unsaturated ethers containing halogen
- C07C43/174—Unsaturated ethers containing halogen containing six-membered aromatic rings
- C07C43/1742—Unsaturated ethers containing halogen containing six-membered aromatic rings with halogen atoms bound to the aromatic rings
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- C07C43/14—Unsaturated ethers
- C07C43/178—Unsaturated ethers containing hydroxy or O-metal groups
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- C07C59/40—Unsaturated compounds
- C07C59/42—Unsaturated compounds containing hydroxy or O-metal groups
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Abstract
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Claims (10)
- 하기 일반식(Ⅱ)의 (2)-아릴프로펜산.상기식에서,기는 케토기로 전활될 수 있는 기로서, 특히, R1는 R2는 동일하거나 상이한 것으로서, 각각 수소, 하이드록실, 최대 10개의 탄소 자를 갖는 알콕시, 5 내지 10개의 탄소 원자를 갖는 사이클로알콕시, 7 내지 12개의 탄소 원자를 갖는 아랄콕시 또는 6 내지 10개의 탄소 원자를 갖는 아릴옥시기(이 기들은 비치환되거나 또는 각각 1 내지 5개의 탄소 원자를 갖는 알킬 또는 알콕시에 의하여 치환됨)를 나타내거나, 또는 O2CR3기(여기서 R3은 수소, 최대 10개의 탄소 원자를 갖는 알킬, 5 내지 10개의 탄소 원자를 갖는 사이클로알킬, 7 내지 12개의 탄소 원자를 갖는 아랄킬 또는 6 내지 10개의 탄소 원자를 갖는 아릴이고, 비치환되거나 각각 1 내지 5개의 탄소 원자를 갖는 알킬 또는 알콕시에 의하여 치환됨)를 나타내거나, 또는 OSiR4R5R6기(여기서, R4, R5및 R6은 서로 독립적으로 각각 R3에서 정의된 바와 같음)를 나타내거나, 또는 NR7R8기(여기서, R7및 R8이 서로 독립적으로 R3에서 정의된 바와 같음)를 나타내거나, 또는 2-테트라하이드로피릴기를 나타내거나, 또는 R1및 R2는 함께；(여기서, D1및 D2는 서로 독립적으로 각각 산소, 황, 또는 NR3기(여기서, R3은 상기 정의된 바와 같음)를 나타내고, n은 1,2 또는 3을 나타냄) 구조의 기를 나타낸다.
- 제1항에 있어서, R1및 R2가 동일하거나 상이한 것으로서 각가 수소, 하이드록실, 1 내지 4개의 탄소 원자를 갖는 알콕시, 벤질옥시, 아세틸옥시, 벤조일옥시, 알킬기가 각각 1 내지 4개의 탄소 원자를 갖는 트리(알킬)실릴, 알킬기가 각각 1 내지 4개의 탄소 원자를 갖는 디알킬아미노 또는 2-테트라하이드로피릴을 나타내거나, 또는 R1및 R2가 함께 -O(CH2)n-CH2-D2-기(여기서 n은 1,2 또는 3을 나타내고, D2는 산소 또는 1 내지 4개의 탄소 원자를 갖는 알킬아민을 나타냄)를 나타내는 일반식(Ⅱ)의 화합물.
- (A) 하기 일반식(III)의 화합물을 통상적인 방법에 의하여 탈수시키거나 또는 (B) 하기 일반식(Ⅳ)의 화합물을 통상적인 방법에 의하여 가수분해시키는 것을 특징으로 하는, 제1항에 따른 일반식(Ⅱ)의 화합물의 제조방법.상기 식에서, R1및 R2는 제1항에서 정의한 바와 같고, R9는 비치환되거나 또는 각각 1 내지 5개의 탄소 원자를 갖는 알킬 또는 알콕시에 의하여 치환되는 1 내지 10개의 탄소 원자를 갖는 알콕시, 5 내지 10개의 탄소 원자를 갖는 사이클로알콕시, 7내지 12개의 탄소 원자를 갖는 아랄콕시 또는 6 내지 10개의 탄소 원자를 갖는 아릴옥시를 나타낸다.
- 일반식(Ⅱ)의 화합물을 키랄 전이 금속 착물로 이루어진 촉매의 존재 하 및 불활성 유기 용매의 존재 또는 부재 하에 수소화 반응시켜 하기 일반식(Ⅰ)의 화합물을 얻고, 이어서 CR1R2기를 통상적인 방법에 의하여 케토기로 전환시키는 것을 특징으로 하는, (S)-케토프로펜의 제조를 위한 제1항에 따른 일반식(Ⅱ)의 화합물의 용도.상기 식에서, R1및 R2는 제1항에서 정의된 바와 같으나, 동시에 수소를 나타내지 않는다.
- 하기 일반식(Ⅰ)의 화합물.상기식에서, R1및 R2는 제1항에서 정의된 바와 같으나, 동시에 수소를 나타내지 않는다.
- 하기 일반식(Ⅲ)의 화합물.상기식에서, R1및 R2는 제1항에서 정의된 바와 같다.
- 하기 일반식(Ⅳ)의 화합물.상기 식에서, R1및 R2는 제1항에서 정의된 바와 같고, R9는 비치환되거나 또는 각각 1 내지 5개의 탄소 원자를 갖는 알킬 또는 알콕시에 의하여 치환되는 1 내지 10개의 탄소 원자를 갖는 알콕시, 5 내지 10개의 탄소 원자를 갖는 사이클로알콕시, 7내지 12개의 탄소 원자를 갖는 아랄콕시 또는 6 내지 10개의 탄소 원자를 갖는 아릴옥시를 나타낸다.
- 하기 일반식(Ⅴ)의 화합물을 25 내지 160℃의 온도에서 불활성 비양자성 용매의 존재 또는 부재 하에, 1내지 200바아의 압력에서 촉매로서 목탄 기재 팔라듐, 및 일산화탄소의 존재하에 알코올과 반응시키고, 무기산을 첨가시키는 것을 특징으로 하는, 알기 일반식(Ⅳ)의 화합물의 제조 방법.상기 식에서, R1및 R2는 제1항에서 정의된 바와 같고, R9는 비치환되거나 또는 각각 1 내지 5개의 탄소 원자를 갖는 알킬 또는 알콕시에 의하여 치환되는 1 내지 10개의 탄소 원자를 갖는 알콕시, 5 내지 10개의 탄소 원자를 갖는 사이클로알콕시, 7내지 12개의 탄소 원자를 갖는 아랄콕시 또는 6 내지 10개의 탄소 원자를 갖는 아릴옥시를 나타낸다.
- 하기 일반식(Ⅳ)의 그리냐르(Grignard) 화합물을 -10 내지 +120℃의 온도에서 유기 용매의 존재하에 하기 일반식(Ⅶ)의 금속 피루베이트와 반응시키는 것을 특징으로 하는, 하기 일반식(Ⅲ)의 화합물의 제조방법.상기 식에서, R1및 R2는 제1항에서 정의된 바와 같고, HAL는 불소, 요오드, 염소 또는 부롬을 나타내고, ME는 알카리금속, 알카리토금속(단량) 또는 MGBR1을 나타낸다.
- (S)-케토프로펜의 대조를 위한 일반식(Ⅰ)의 화합물의 용도.※참고사항:최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4128787A DE4128787A1 (de) | 1991-08-30 | 1991-08-30 | Neue zwischenprodukte und ihre verwendung bei der herstellung von s-ketoprofen |
| DEP4128787.8 | 1991-08-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR930004245A true KR930004245A (ko) | 1993-03-22 |
Family
ID=6439458
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019920015637A KR930004245A (ko) | 1991-08-30 | 1992-08-29 | 신규 중간체 및 s-케토프로펜의 제조에 있어서의 그의 용도 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US5362907A (ko) |
| EP (1) | EP0529444B1 (ko) |
| JP (1) | JPH05279293A (ko) |
| KR (1) | KR930004245A (ko) |
| AT (1) | ATE151736T1 (ko) |
| CA (1) | CA2077000A1 (ko) |
| DE (2) | DE4128787A1 (ko) |
| ES (1) | ES2100257T3 (ko) |
| FI (1) | FI923842A (ko) |
| HU (1) | HUT63599A (ko) |
| TW (1) | TW213450B (ko) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10212301A1 (de) | 2002-03-20 | 2003-10-02 | Bayer Ag | Verfahren zur Herstellung von Aryl-aminopropanolen |
| US20050079454A1 (en) * | 2003-10-14 | 2005-04-14 | Best Leroy E. | Contrast enhancement materials containing non-PFOS surfactants |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1546478A (fr) * | 1967-01-27 | 1968-11-22 | Rhone Poulenc Sa | Nouveaux dérivés de l'acide benzoyl-3 phénylacétique et leur préparation |
| ES446581A1 (es) * | 1975-04-04 | 1977-06-16 | Boots Co Ltd | Un procedimiento para preparar acidos 2-arilpropionicos. |
| JPS54117404A (en) * | 1978-03-06 | 1979-09-12 | Sagami Chem Res Center | Reductive desulfurization of sulfides |
| JPS54148761A (en) * | 1978-05-16 | 1979-11-21 | Takayuki Shioiri | Novel 22*33*alphaahydroxybenzyl*phenyl* propionic acid and its manufacture |
| JPS552614A (en) * | 1978-06-21 | 1980-01-10 | Ota Seiyaku Kk | Preparation of 2-artl alkane acid |
| JPH064561B2 (ja) * | 1986-02-08 | 1994-01-19 | 日本石油化学株式会社 | （置換アリ−ル）カルボン酸の製造方法 |
| JPS62265293A (ja) * | 1986-05-13 | 1987-11-18 | Takasago Corp | ルテニウム−ホスフイン錯体 |
| DE3778857D1 (de) * | 1986-11-14 | 1992-06-11 | Takasago Perfumery Co Ltd | Katalytische produktion von optisch aktiven carbonsaeuren. |
| US4962124A (en) * | 1987-11-17 | 1990-10-09 | Analgesic Associates | Onset-hastened/enhanced antipyretic response |
| DE3824353A1 (de) * | 1988-07-19 | 1990-01-25 | Paz Arzneimittelentwicklung | Verfahren zur trennung von gemischen enantiomerer arylpropionsaeuren |
| JPH0757758B2 (ja) * | 1988-10-24 | 1995-06-21 | 高砂香料工業株式会社 | ルテニウム―ホスフィン錯体 |
| JPH0623150B2 (ja) * | 1988-11-15 | 1994-03-30 | 高砂香料工業株式会社 | 光学活性３−ヒドロキシブタン酸類の製造方法 |
| EP0379917B1 (de) * | 1989-01-26 | 1995-08-09 | Bayer Ag | Optisch aktive (Meth)Acrylsäure-Derivate, ihre Herstellung, ihre Polymerisation zu optisch aktiven Polymeren und deren Verwendung |
| ATE128140T1 (de) * | 1989-05-18 | 1995-10-15 | Hoffmann La Roche | Phosphorverbindungen. |
| JPH0733392B2 (ja) * | 1989-06-16 | 1995-04-12 | 高砂香料工業株式会社 | ２，２’―ビス〔ジー（ｍ―トリル）ホスフィノ〕―１，１’―ビナフチル |
| FR2651494B1 (fr) * | 1989-09-05 | 1993-01-08 | Rhone Poulenc Sante | Procede de preparation d'acides aryl-2 propioniques optiquement actifs. |
-
1991
- 1991-08-30 DE DE4128787A patent/DE4128787A1/de not_active Withdrawn
-
1992
- 1992-07-31 TW TW081106051A patent/TW213450B/zh active
- 1992-08-17 DE DE59208349T patent/DE59208349D1/de not_active Expired - Fee Related
- 1992-08-17 EP EP92113945A patent/EP0529444B1/de not_active Expired - Lifetime
- 1992-08-17 AT AT92113945T patent/ATE151736T1/de not_active IP Right Cessation
- 1992-08-17 ES ES92113945T patent/ES2100257T3/es not_active Expired - Lifetime
- 1992-08-21 US US07/934,044 patent/US5362907A/en not_active Expired - Fee Related
- 1992-08-27 FI FI923842A patent/FI923842A/fi unknown
- 1992-08-27 CA CA002077000A patent/CA2077000A1/en not_active Abandoned
- 1992-08-28 JP JP4251936A patent/JPH05279293A/ja active Pending
- 1992-08-29 HU HU9202787A patent/HUT63599A/hu unknown
- 1992-08-29 KR KR1019920015637A patent/KR930004245A/ko not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| TW213450B (ko) | 1993-09-21 |
| EP0529444B1 (de) | 1997-04-16 |
| ATE151736T1 (de) | 1997-05-15 |
| FI923842A0 (fi) | 1992-08-27 |
| EP0529444A2 (de) | 1993-03-03 |
| DE4128787A1 (de) | 1993-03-04 |
| FI923842A (fi) | 1993-03-01 |
| JPH05279293A (ja) | 1993-10-26 |
| CA2077000A1 (en) | 1993-03-01 |
| HU9202787D0 (en) | 1992-12-28 |
| EP0529444A3 (en) | 1994-09-07 |
| ES2100257T3 (es) | 1997-06-16 |
| DE59208349D1 (de) | 1997-05-22 |
| HUT63599A (en) | 1993-09-28 |
| US5362907A (en) | 1994-11-08 |
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