JPH07507277A - ピペリジンジオン誘導体の立体特異的加水分解方法 - Google Patents
ピペリジンジオン誘導体の立体特異的加水分解方法Info
- Publication number
- JPH07507277A JPH07507277A JP5519022A JP51902293A JPH07507277A JP H07507277 A JPH07507277 A JP H07507277A JP 5519022 A JP5519022 A JP 5519022A JP 51902293 A JP51902293 A JP 51902293A JP H07507277 A JPH07507277 A JP H07507277A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- isomer
- paroxetine
- esterase
- 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
- 238000000034 method Methods 0.000 title claims description 33
- 230000007062 hydrolysis Effects 0.000 title description 3
- 238000006460 hydrolysis reaction Methods 0.000 title description 3
- 229940053994 hypnotics and sedatives piperidinedione derivative Drugs 0.000 title description 3
- 150000005458 piperidinediones Chemical class 0.000 title description 3
- 230000000707 stereoselective effect Effects 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 39
- 238000006243 chemical reaction Methods 0.000 claims description 11
- AHOUBRCZNHFOSL-YOEHRIQHSA-N (+)-Casbol Chemical compound C1=CC(F)=CC=C1[C@H]1[C@H](COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-YOEHRIQHSA-N 0.000 claims description 10
- 108010051152 Carboxylesterase Proteins 0.000 claims description 10
- 102000013392 Carboxylesterase Human genes 0.000 claims description 10
- AHOUBRCZNHFOSL-UHFFFAOYSA-N Paroxetine hydrochloride Natural products C1=CC(F)=CC=C1C1C(COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-UHFFFAOYSA-N 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- 229960002296 paroxetine Drugs 0.000 claims description 10
- 108090000371 Esterases Proteins 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 210000004185 liver Anatomy 0.000 claims description 7
- 239000012453 solvate Substances 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- 239000003125 aqueous solvent Substances 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 239000003791 organic solvent mixture Substances 0.000 claims description 3
- 108090000790 Enzymes Proteins 0.000 claims description 2
- 102000004190 Enzymes Human genes 0.000 claims description 2
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000000468 ketone group Chemical group 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000003386 piperidinyl group Chemical group 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 239000001301 oxygen Substances 0.000 claims 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 241000283690 Bos taurus Species 0.000 claims 1
- 230000032050 esterification Effects 0.000 claims 1
- 238000005886 esterification reaction Methods 0.000 claims 1
- CEXCHYIGFUAPKW-UHFFFAOYSA-N methanol;piperidine Chemical compound OC.C1CCNCC1 CEXCHYIGFUAPKW-UHFFFAOYSA-N 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 5
- -1 hydrochloride Chemical class 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical group OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 3
- 230000003110 anti-inflammatory effect Effects 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 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 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 108010070880 sigma K Proteins 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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 directly attached to ring carbon atoms
- C07D211/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9209687.4 | 1992-05-06 | ||
| GB929209687A GB9209687D0 (en) | 1992-05-06 | 1992-05-06 | Novel process |
| PCT/GB1993/000721 WO1993022284A1 (en) | 1992-05-06 | 1993-04-06 | Process for stereospecific hydrolysis of piperidinedione derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH07507277A true JPH07507277A (ja) | 1995-08-10 |
Family
ID=10715029
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5519022A Pending JPH07507277A (ja) | 1992-05-06 | 1993-04-06 | ピペリジンジオン誘導体の立体特異的加水分解方法 |
Country Status (32)
| Country | Link |
|---|---|
| US (1) | US20010018205A1 (en, 2012) |
| EP (1) | EP0639180B1 (en, 2012) |
| JP (1) | JPH07507277A (en, 2012) |
| KR (1) | KR100287082B1 (en, 2012) |
| CN (2) | CN1059898C (en, 2012) |
| AP (1) | AP404A (en, 2012) |
| AT (1) | ATE194329T1 (en, 2012) |
| AU (1) | AU673166B2 (en, 2012) |
| BR (1) | BR9306326A (en, 2012) |
| CA (1) | CA2135169A1 (en, 2012) |
| CZ (1) | CZ283702B6 (en, 2012) |
| DE (1) | DE69328969T2 (en, 2012) |
| DK (1) | DK0639180T3 (en, 2012) |
| ES (1) | ES2147196T3 (en, 2012) |
| FI (1) | FI106855B (en, 2012) |
| GB (1) | GB9209687D0 (en, 2012) |
| GR (1) | GR3034034T3 (en, 2012) |
| HU (1) | HU215411B (en, 2012) |
| IL (1) | IL105162A (en, 2012) |
| MA (1) | MA22848A1 (en, 2012) |
| MX (1) | MX9301754A (en, 2012) |
| MY (1) | MY110188A (en, 2012) |
| NO (1) | NO944215L (en, 2012) |
| NZ (1) | NZ251404A (en, 2012) |
| PL (1) | PL172067B1 (en, 2012) |
| PT (1) | PT639180E (en, 2012) |
| RU (1) | RU2108393C1 (en, 2012) |
| SI (1) | SI9300158A (en, 2012) |
| SK (1) | SK281767B6 (en, 2012) |
| TW (1) | TW258732B (en, 2012) |
| WO (1) | WO1993022284A1 (en, 2012) |
| ZA (1) | ZA932212B (en, 2012) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001500148A (ja) * | 1996-09-11 | 2001-01-09 | スミスクライン・ビーチャム・パブリック・リミテッド・カンパニー | １―ブチル―４―ピペリジニルメチルアミンの製造 |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9325644D0 (en) * | 1993-12-15 | 1994-02-16 | Smithkline Beecham Plc | Novel formulation |
| EP0937152A2 (en) * | 1996-07-15 | 1999-08-25 | Smithkline Beecham Plc | Screening for and use of an esterase for a stereospecific resolution |
| DE29724281U1 (de) | 1997-06-10 | 2000-08-10 | Synthon Bv | 4-Phenylpiperidin-Verbindungen |
| CH689805A8 (fr) * | 1998-07-02 | 2000-02-29 | Smithkline Beecham Plc | Méthanesulfonate de paroxétine, procédé pour sa préparation et compositions pharmaceutiques le contenant. |
| IT1308629B1 (it) | 1999-02-23 | 2002-01-09 | Recordati Chem Pharm | Processo per la produzione di paroxetina. |
| ES2161167B1 (es) * | 1999-09-24 | 2002-07-01 | Vita Invest Sa | Procedimiento de hidrolisis enzimatica de esteres del acido (3sr,4rs)-4-(4-fluorofenil)-6-oxopiperidin-3-carboxilico con biocatalizadores de lipasas o esterasas inmovilizadas. |
| AU2000246280A1 (en) | 2000-05-12 | 2001-11-20 | Synthon B.V. | Tosylate salts of 4-(p-fluorophenyl)-piperidine-3-carbinols |
| WO2009005647A2 (en) * | 2007-06-27 | 2009-01-08 | Bioverdant, Inc. | Compounds and process to prepare chiral intermediates for synthesis of paroxetine |
| CN104892491B (zh) * | 2015-05-06 | 2017-05-17 | 浙江海森药业有限公司 | 一种合成帕罗西汀手性中间体的方法 |
| KR102168129B1 (ko) | 2018-11-28 | 2020-10-20 | 장영선 | 넝쿨작물용 줄기 유인용 집게 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1422263A (en) * | 1973-01-30 | 1976-01-21 | Ferrosan As | 4-phenyl-piperidine compounds |
| DE3010104A1 (de) * | 1980-03-15 | 1981-10-01 | Basf Ag, 6700 Ludwigshafen | Aminoazoverbindungen |
| DE3680184D1 (de) * | 1985-08-10 | 1991-08-14 | Beecham Group Plc | Verfahren zur herstellung von arylpiperidincarbinol. |
| EP0223403B1 (en) * | 1985-10-25 | 1993-08-04 | Beecham Group Plc | Piperidine derivative, its preparation, and its use as medicament |
| DK716088D0 (da) * | 1988-12-22 | 1988-12-22 | Ferrosan As | Reduktion af piperidin-dion-derivater samt intermediat |
| US5258517A (en) * | 1992-08-06 | 1993-11-02 | Sepracor, Inc. | Method of preparing optically pure precursors of paroxetine |
-
1992
- 1992-05-06 GB GB929209687A patent/GB9209687D0/en active Pending
-
1993
- 1993-03-25 IL IL10516293A patent/IL105162A/en not_active IP Right Cessation
- 1993-03-25 AP APAP/P/1993/000501A patent/AP404A/en active
- 1993-03-29 MX MX9301754A patent/MX9301754A/es not_active IP Right Cessation
- 1993-03-29 ZA ZA932212A patent/ZA932212B/xx unknown
- 1993-03-31 MY MYPI93000567A patent/MY110188A/en unknown
- 1993-03-31 SI SI9300158A patent/SI9300158A/sl unknown
- 1993-03-31 MA MA23143A patent/MA22848A1/fr unknown
- 1993-04-01 CN CN93104523A patent/CN1059898C/zh not_active Expired - Fee Related
- 1993-04-06 AT AT93908004T patent/ATE194329T1/de not_active IP Right Cessation
- 1993-04-06 PT PT93908004T patent/PT639180E/pt unknown
- 1993-04-06 DK DK93908004T patent/DK0639180T3/da active
- 1993-04-06 BR BR9306326A patent/BR9306326A/pt not_active Application Discontinuation
- 1993-04-06 ES ES93908004T patent/ES2147196T3/es not_active Expired - Lifetime
- 1993-04-06 AU AU38999/93A patent/AU673166B2/en not_active Ceased
- 1993-04-06 EP EP93908004A patent/EP0639180B1/en not_active Expired - Lifetime
- 1993-04-06 JP JP5519022A patent/JPH07507277A/ja active Pending
- 1993-04-06 CA CA002135169A patent/CA2135169A1/en not_active Abandoned
- 1993-04-06 RU RU94046012A patent/RU2108393C1/ru active
- 1993-04-06 HU HU9403189A patent/HU215411B/hu not_active IP Right Cessation
- 1993-04-06 NZ NZ251404A patent/NZ251404A/en unknown
- 1993-04-06 SK SK1315-94A patent/SK281767B6/sk unknown
- 1993-04-06 DE DE69328969T patent/DE69328969T2/de not_active Expired - Fee Related
- 1993-04-06 CZ CZ942712A patent/CZ283702B6/cs not_active IP Right Cessation
- 1993-04-06 PL PL93305801A patent/PL172067B1/pl unknown
- 1993-04-06 WO PCT/GB1993/000721 patent/WO1993022284A1/en active IP Right Grant
- 1993-04-14 TW TW082102827A patent/TW258732B/zh active
-
1994
- 1994-11-04 FI FI945209A patent/FI106855B/fi active
- 1994-11-04 NO NO944215A patent/NO944215L/no not_active Application Discontinuation
- 1994-11-05 KR KR1019940703956A patent/KR100287082B1/ko not_active Expired - Fee Related
-
2000
- 2000-04-03 CN CN00104973A patent/CN1291653A/zh active Pending
- 2000-07-27 GR GR20000401724T patent/GR3034034T3/el not_active IP Right Cessation
-
2001
- 2001-03-21 US US09/813,755 patent/US20010018205A1/en not_active Abandoned
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001500148A (ja) * | 1996-09-11 | 2001-01-09 | スミスクライン・ビーチャム・パブリック・リミテッド・カンパニー | １―ブチル―４―ピペリジニルメチルアミンの製造 |
| JP2005220126A (ja) * | 1996-09-11 | 2005-08-18 | Smithkline Beecham Plc | １−ブチル−４−ピペリジニルメチルアミンの製造法 |
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