JP2003527374A5 - - Google Patents
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- Publication number
- JP2003527374A5 JP2003527374A5 JP2001567703A JP2001567703A JP2003527374A5 JP 2003527374 A5 JP2003527374 A5 JP 2003527374A5 JP 2001567703 A JP2001567703 A JP 2001567703A JP 2001567703 A JP2001567703 A JP 2001567703A JP 2003527374 A5 JP2003527374 A5 JP 2003527374A5
- Authority
- JP
- Japan
- Prior art keywords
- mixture
- added
- dimethoxybenzyl
- isoquinolin
- acetamide
- 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.)
- Granted
Links
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 3
- 230000001808 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- SGHBDLOMRUXKQF-UIOOFZCWSA-N N-[(1S)-2,3-dihydro-1H-inden-1-yl]-2-[(1S)-1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl]acetamide Chemical compound C1=C(OC)C(OC)=CC=C1C[C@H]1C2=CC(OC)=C(OC)C=C2CCN1CC(=O)N[C@@H]1C2=CC=CC=C2CC1 SGHBDLOMRUXKQF-UIOOFZCWSA-N 0.000 description 1
- UWYZHKAOTLEWKK-UHFFFAOYSA-N Tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 description 1
- 150000001347 alkyl bromides Chemical class 0.000 description 1
- CKDWPUIZGOQOOM-UHFFFAOYSA-N carbamoyl chloride Chemical class NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000005712 crystallization Effects 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- -1 heteroaryl chlorides Chemical class 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
Description
C. フェノールと臭化アルキル、塩化ヘテロアリール、ヘテロアリール-メチル-スルホン及び塩化カルバモイルとのカップリング
C.1 出発物質:ベンジルエーテルの脱保護:
パラジウム(10% Pd/C、wet, 274 mg)を、メタノール(60 mL)及びギ酸(11.0 mL)の混合液に添加した。各ベンジルエーテル(4.0 mmol)を少量に分けて添加し、その混合液を40時間攪拌した。この間、出発物質が消費されるまでPd/Cを更に添加した。混合液をろ過し、溶媒を真空下で除去した後、残渣をフラッシュ・クロマトグラフィーにより精製
し、以下のフェノールを得た。
C.1 出発物質:ベンジルエーテルの脱保護:
パラジウム(10% Pd/C、wet, 274 mg)を、メタノール(60 mL)及びギ酸(11.0 mL)の混合液に添加した。各ベンジルエーテル(4.0 mmol)を少量に分けて添加し、その混合液を40時間攪拌した。この間、出発物質が消費されるまでPd/Cを更に添加した。混合液をろ過し、溶媒を真空下で除去した後、残渣をフラッシュ・クロマトグラフィーにより精製
し、以下のフェノールを得た。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP00/02245 | 2000-03-14 | ||
EP0002245 | 2000-03-14 | ||
PCT/EP2001/002733 WO2001068609A1 (en) | 2000-03-14 | 2001-03-12 | 1,2,3,4-tetrahydroisoquinoline derivatives |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2003527374A JP2003527374A (ja) | 2003-09-16 |
JP2003527374A5 true JP2003527374A5 (ja) | 2007-09-06 |
JP4009460B2 JP4009460B2 (ja) | 2007-11-14 |
Family
ID=8163870
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2001567703A Expired - Lifetime JP4009460B2 (ja) | 2000-03-14 | 2001-03-12 | 1,2,3,4−テトラヒドロイソキノリン誘導体 |
Country Status (18)
Country | Link |
---|---|
US (1) | US6703392B2 (ja) |
JP (1) | JP4009460B2 (ja) |
KR (2) | KR20070087103A (ja) |
CN (1) | CN100393703C (ja) |
AT (1) | ATE286500T1 (ja) |
AU (2) | AU2001260113B2 (ja) |
BR (1) | BRPI0109200B8 (ja) |
CA (1) | CA2402431C (ja) |
DE (1) | DE60108236T2 (ja) |
ES (1) | ES2234840T3 (ja) |
HU (1) | HU227811B1 (ja) |
IL (2) | IL150986A0 (ja) |
MX (1) | MXPA02008797A (ja) |
NO (1) | NO324932B1 (ja) |
NZ (1) | NZ520624A (ja) |
PT (1) | PT1274687E (ja) |
WO (1) | WO2001068609A1 (ja) |
ZA (1) | ZA200206467B (ja) |
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JPH07267961A (ja) * | 1994-03-30 | 1995-10-17 | Taisho Pharmaceut Co Ltd | ベンゾフロ[3,2−dピリミジン−4−オン誘導体 |
JPH1095766A (ja) * | 1996-09-19 | 1998-04-14 | Sanwa Kagaku Kenkyusho Co Ltd | アセトアミド誘導体、及びその用途 |
SK65499A3 (en) * | 1996-11-27 | 2001-05-10 | Pfizer | Apo b-secretion/mtp inhibitory amides |
AR016817A1 (es) | 1997-08-14 | 2001-08-01 | Smithkline Beecham Plc | Derivados de fenilurea o feniltiourea, procedimiento para su preparacion, coleccion de compuestos, compuestos intermediarios, composicion farmaceutica,metodo de tratamiento y uso de dichos compuestos para la manufactura de un medicamento |
AU4037799A (en) * | 1998-05-08 | 1999-11-29 | Smithkline Beecham Plc | Phenylurea and phenylthio urea derivatives |
WO2000029399A1 (en) | 1998-11-12 | 2000-05-25 | Boehringer Ingelheim (Canada) Ltd. | Antiherpes compounds |
GB9827467D0 (en) | 1998-12-15 | 1999-02-10 | Zeneca Ltd | Chemical compounds |
GB9914015D0 (en) | 1999-06-17 | 1999-08-18 | Zeneca Ltd | Chemical compounds |
GB9914025D0 (en) | 1999-06-17 | 1999-08-18 | Zeneca Ltd | Chemical compounds |
AU6073300A (en) | 1999-07-06 | 2001-01-22 | Vertex Pharmaceuticals Incorporated | N-heterocyclic derivatives with neuronal activity |
-
2001
- 2001-03-12 BR BRPI0109200A patent/BRPI0109200B8/pt not_active IP Right Cessation
- 2001-03-12 KR KR1020077016214A patent/KR20070087103A/ko active Search and Examination
- 2001-03-12 CN CNB018063268A patent/CN100393703C/zh not_active Expired - Lifetime
- 2001-03-12 ES ES01933685T patent/ES2234840T3/es not_active Expired - Lifetime
- 2001-03-12 WO PCT/EP2001/002733 patent/WO2001068609A1/en active IP Right Grant
- 2001-03-12 US US10/239,693 patent/US6703392B2/en not_active Expired - Lifetime
- 2001-03-12 HU HU0300207A patent/HU227811B1/hu unknown
- 2001-03-12 PT PT01933685T patent/PT1274687E/pt unknown
- 2001-03-12 CA CA002402431A patent/CA2402431C/en not_active Expired - Lifetime
- 2001-03-12 AU AU2001260113A patent/AU2001260113B2/en not_active Expired
- 2001-03-12 NZ NZ520624A patent/NZ520624A/xx not_active IP Right Cessation
- 2001-03-12 JP JP2001567703A patent/JP4009460B2/ja not_active Expired - Lifetime
- 2001-03-12 DE DE60108236T patent/DE60108236T2/de not_active Expired - Lifetime
- 2001-03-12 IL IL15098601A patent/IL150986A0/xx active IP Right Grant
- 2001-03-12 AU AU6011301A patent/AU6011301A/xx active Pending
- 2001-03-12 KR KR1020027011533A patent/KR100842698B1/ko active IP Right Grant
- 2001-03-12 MX MXPA02008797A patent/MXPA02008797A/es active IP Right Grant
- 2001-03-12 AT AT01933685T patent/ATE286500T1/de active
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2002
- 2002-07-30 IL IL150986A patent/IL150986A/en unknown
- 2002-08-13 ZA ZA200206467A patent/ZA200206467B/en unknown
- 2002-09-11 NO NO20024339A patent/NO324932B1/no not_active IP Right Cessation
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