JP2003527374A5 - - Google Patents
Download PDFInfo
- 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) | AU6011301A (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) |
Families Citing this family (92)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AU2002224885A1 (en) * | 2000-11-28 | 2002-06-11 | Smithkline Beecham Plc | Morpholine derivatives as antagonists of orexin receptors |
GB0126292D0 (en) * | 2001-11-01 | 2002-01-02 | Smithkline Beecham Plc | Compounds |
GB0130388D0 (en) * | 2001-12-19 | 2002-02-06 | Smithkline Beecham Plc | Compounds |
US7105526B2 (en) | 2002-06-28 | 2006-09-12 | Banyu Pharmaceuticals Co., Ltd. | Benzimidazole derivatives |
CA2498091C (en) | 2002-10-11 | 2011-03-22 | Actelion Pharmaceuticals Ltd. | Sulfonylamino-acetic acid derivatives |
GB0225884D0 (en) * | 2002-11-06 | 2002-12-11 | Glaxo Group Ltd | Novel compounds |
US7772188B2 (en) | 2003-01-28 | 2010-08-10 | Ironwood Pharmaceuticals, Inc. | Methods and compositions for the treatment of gastrointestinal disorders |
EP1599206A4 (en) * | 2003-02-24 | 2008-05-21 | Merck & Co Inc | MODULATORS OF HETEROTRICYLICAMIDE FUSIONED WITH AMINOCYCLOPENTYL OF ACTIVITY OF CHEMOKINE RECEPTORS |
CN100432056C (zh) * | 2003-03-26 | 2008-11-12 | 埃科特莱茵药品有限公司 | 四氢异喹啉基乙酰胺衍生物作为阿立新受体拮抗剂的应用 |
US7321065B2 (en) * | 2003-04-18 | 2008-01-22 | The Regents Of The University Of California | Thyronamine derivatives and analogs and methods of use thereof |
CN1780820A (zh) | 2003-04-28 | 2006-05-31 | 埃科特莱茵药品有限公司 | 作为阿立新受体拮抗剂的喹喔啉-3-酮衍生物 |
ATE547404T1 (de) | 2003-09-22 | 2012-03-15 | Msd Kk | Piperidinderivate |
US20100048513A1 (en) | 2008-08-20 | 2010-02-25 | Hawkins Michael J | Novel inhibitors of chymase |
EP1716160B1 (en) * | 2004-01-23 | 2010-12-29 | Janssen Pharmaceutica NV | Novel inhibitors of chymase |
WO2005118548A1 (en) * | 2004-03-01 | 2005-12-15 | Actelion Pharmaceuticals Ltd | Substituted 1,2,3,4-tetrahydroisoquinoline derivatives |
US20080125403A1 (en) | 2004-04-02 | 2008-05-29 | Merck & Co., Inc. | Method of Treating Men with Metabolic and Anthropometric Disorders |
EP2286837A3 (en) | 2004-11-01 | 2013-09-04 | Amylin Pharmaceuticals, LLC | Treatment of obesity and obesity related diseases |
WO2006081522A2 (en) * | 2005-01-26 | 2006-08-03 | The Regents Of The Unversity Of California | Modulation of nmda receptor currents via orexin receptor and/or crf receptor |
WO2007022123A2 (en) | 2005-08-11 | 2007-02-22 | Amylin Pharmaceuticals, Inc. | Hybrid polypeptides with selectable properties |
US7501395B2 (en) | 2005-04-25 | 2009-03-10 | Eisai R & D Management Co., Ltd. | Method of screening for antianxiety drugs |
US7737155B2 (en) | 2005-05-17 | 2010-06-15 | Schering Corporation | Nitrogen-containing heterocyclic compounds and methods of use thereof |
NZ562766A (en) | 2005-05-30 | 2011-03-31 | Banyu Pharma Co Ltd | Piperidine derivatives as histamine-H3 receptor antagonists |
JPWO2007018248A1 (ja) | 2005-08-10 | 2009-02-19 | 萬有製薬株式会社 | ピリドン化合物 |
EP2330125A3 (en) | 2005-08-11 | 2012-12-12 | Amylin Pharmaceuticals, Inc. | Hybrid polypeptides with selectable properties |
US7875633B2 (en) | 2005-08-24 | 2011-01-25 | Banyu Pharmaceutical Co., Ltd. | Phenylpyridone derivative |
JPWO2007029847A1 (ja) | 2005-09-07 | 2009-03-19 | 萬有製薬株式会社 | 二環性芳香族置換ピリドン誘導体 |
AU2006297443B2 (en) | 2005-09-29 | 2010-08-12 | Merck Sharp & Dohme Corp. | Acylated spiropiperidine derivatives as melanocortin-4 receptor modulators |
BRPI0617621A2 (pt) | 2005-10-21 | 2011-08-02 | Novartis Ag | combinação de compostos orgánicos |
JPWO2007049798A1 (ja) | 2005-10-27 | 2009-04-30 | 萬有製薬株式会社 | 新規ベンゾオキサチイン誘導体 |
NZ568292A (en) | 2005-11-10 | 2011-08-26 | Msd Kk | Spiro[cyclohexane-1,1'-(3'H)-4'-azaisobenzofuran]-4-carboxamide derivatives |
EP1981881B1 (en) * | 2006-01-26 | 2011-12-07 | Actelion Pharmaceuticals Ltd. | Tetrahydropyrane antibiotics |
MX2008011647A (es) * | 2006-03-15 | 2008-09-22 | Actelion Pharmaceuticals Ltd | Derivados de tetrahidroisoquinolina para mejorar la funcion de la memoria. |
AU2007238755B2 (en) | 2006-04-12 | 2012-07-12 | Merck Sharp & Dohme Llc | Pyridyl amide T-type calcium channel antagonists |
EP2013209B1 (en) | 2006-04-26 | 2011-01-19 | Actelion Pharmaceuticals Ltd. | Pyrazolo-tetrahydropyridine derivatives as orexin receptor antagonists |
CA2657623A1 (en) | 2006-07-14 | 2008-01-17 | Merck & Co., Inc. | Bridged diazepan orexin receptor antagonists |
CA2659352A1 (en) * | 2006-08-28 | 2008-03-06 | Actelion Pharmaceuticals Ltd | 1,4,5,6,7,8-hexahydro-1,2,5-triaza-azulene derivatives as orexin receptor antagonists |
CA2664113C (en) | 2006-09-22 | 2013-05-28 | Merck & Co., Inc. | Use of platencin and platensimycin as fatty acid synthesis inhibitors to treat obesity, diabetes and cancer |
EP2072519A4 (en) | 2006-09-28 | 2009-10-21 | Banyu Pharma Co Ltd | DIARYLKETIMINDERIVAT |
PE20081229A1 (es) | 2006-12-01 | 2008-08-28 | Merck & Co Inc | Antagonistas de receptor de orexina de diazepam sustituido |
AU2007337659A1 (en) | 2006-12-22 | 2008-07-03 | Actelion Pharmaceuticals Ltd. | 5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine derivatives |
CA2682727C (en) | 2007-04-02 | 2016-03-22 | Banyu Pharmaceutical Co., Ltd. | Indoledione derivative |
EP2144906B1 (en) * | 2007-04-04 | 2011-06-15 | F. Hoffmann-La Roche AG | Heterocycles as orexin antagonists |
EP2150114A4 (en) | 2007-05-18 | 2012-01-18 | Merck Sharp & Dohme | OXO-BRIDGED DIAZEPANOREXINE RECEPTOR ANTAGONISTS |
EP2150115B1 (en) | 2007-05-23 | 2013-09-18 | Merck Sharp & Dohme Corp. | Cyclopropyl pyrrolidine orexin receptor antagonists |
RU2470021C2 (ru) | 2007-05-23 | 2012-12-20 | Мерк Шарп Энд Домэ Корп. | Пиридилпиперидиновые антагонисты рецептора орексинов |
EP2170930B3 (en) | 2007-06-04 | 2013-10-02 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders |
US8969514B2 (en) | 2007-06-04 | 2015-03-03 | Synergy Pharmaceuticals, Inc. | Agonists of guanylate cyclase useful for the treatment of hypercholesterolemia, atherosclerosis, coronary heart disease, gallstone, obesity and other cardiovascular diseases |
PE20091010A1 (es) * | 2007-10-10 | 2009-08-08 | Actelion Pharmaceuticals Ltd | Derivados de tetrahidroquinolina |
KR20100072266A (ko) | 2007-10-24 | 2010-06-30 | 머크 샤프 앤드 돔 코포레이션 | 헤테로사이클 페닐 아미드 t-형 칼슘 채널 길항제 |
CN102083796B (zh) * | 2007-12-28 | 2013-06-05 | 埃科特莱茵药品有限公司 | 三取代3,4-二氢-1h-异喹啉化合物,其制备方法,及其用途 |
CA2714617A1 (en) | 2008-03-06 | 2009-09-11 | Banyu Pharmaceutical Co., Ltd. | Alkylaminopyridine derivative |
AU2009229860A1 (en) | 2008-03-28 | 2009-10-01 | Msd K.K. | Diarylmethylamide derivative having antagonistic activity on melanin-concentrating hormone receptor |
CN102149412A (zh) | 2008-05-20 | 2011-08-10 | 纽罗吉斯克斯公司 | 肝脏保护剂对乙酰氨基酚协同前药 |
AU2009261248A1 (en) | 2008-06-19 | 2009-12-23 | Banyu Pharmaceutical Co., Ltd. | Spirodiamine-diarylketoxime derivative |
US20110105514A1 (en) * | 2008-06-25 | 2011-05-05 | Hamed Aissaoui | 5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine compounds |
AU2009270833B2 (en) | 2008-07-16 | 2015-02-19 | Bausch Health Ireland Limited | Agonists of guanylate cyclase useful for the treatment of gastrointestinal, inflammation, cancer and other disorders |
WO2010013595A1 (ja) | 2008-07-30 | 2010-02-04 | 萬有製薬株式会社 | 5員-5員又は5員-6員縮環シクロアルキルアミン誘導体 |
EP2161266A1 (en) | 2008-08-22 | 2010-03-10 | EVOTEC Neurosciences GmbH | Benzofuran derivatives as orexin receptor antagonists |
CN102264228A (zh) | 2008-10-22 | 2011-11-30 | 默沙东公司 | 用于抗糖尿病药的新的环状苯并咪唑衍生物 |
AU2009309037A1 (en) | 2008-10-31 | 2010-05-06 | Merck Sharp & Dohme Corp. | Novel cyclic benzimidazole derivatives useful anti-diabetic agents |
WO2010064212A1 (en) | 2008-12-05 | 2010-06-10 | Actelion Pharmaceuticals Ltd | Method for obtaining an optically pure 1,2,3,4 tetrahydro-isoquinoline derivative |
EP2379562A1 (en) | 2008-12-16 | 2011-10-26 | Schering Corporation | Bicyclic pyranone derivatives as nicotinic acid receptor agonists |
EP2379547A1 (en) | 2008-12-16 | 2011-10-26 | Schering Corporation | Pyridopyrimidine derivatives and methods of use thereof |
WO2011061318A1 (en) | 2009-11-23 | 2011-05-26 | N.V. Organon | Heterocylic compounds as antagonists of the orexin receptors |
AU2011218830B2 (en) | 2010-02-25 | 2014-07-24 | Merck Sharp & Dohme Corp. | Novel cyclic benzimidazole derivatives useful anti-diabetic agents |
WO2011138266A1 (en) | 2010-05-03 | 2011-11-10 | Evotec Ag | Indolizine and imidazopyridine derivatives as orexin receptor antagonists |
WO2011138265A2 (en) | 2010-05-03 | 2011-11-10 | Evotec Ag | Indole and indazole derivatives as orexin receptor antagonists |
EP2402322A1 (en) | 2010-07-02 | 2012-01-04 | Actelion Pharmaceuticals Ltd. | 1,2,3,4-tetrahydroisoquinoline derivative and its use as orexin receptor antagonist |
US9616097B2 (en) | 2010-09-15 | 2017-04-11 | Synergy Pharmaceuticals, Inc. | Formulations of guanylate cyclase C agonists and methods of use |
PE20140859A1 (es) | 2011-02-25 | 2014-07-25 | Merck Sharp & Dohme | Novedosos derivados de azabencimidazol ciclico utiles como agentes antidiabeticos |
BR112014003704A2 (pt) | 2011-09-19 | 2017-03-07 | Eth Zuerich | moduladores ror gama |
AR088352A1 (es) | 2011-10-19 | 2014-05-28 | Merck Sharp & Dohme | Antagonistas del receptor de 2-piridiloxi-4-nitrilo orexina |
WO2013078413A1 (en) * | 2011-11-22 | 2013-05-30 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Modulators of lipid storage |
JP2015525782A (ja) | 2012-08-02 | 2015-09-07 | メルク・シャープ・アンド・ドーム・コーポレーションMerck Sharp & Dohme Corp. | 抗糖尿病性三環式化合物 |
PT2935222T (pt) | 2012-12-21 | 2018-12-10 | Epizyme Inc | Inibidores de prmt5 e seus usos |
EP2958562A4 (en) | 2013-02-22 | 2016-08-10 | Merck Sharp & Dohme | BICYCLIC ANTIDIABETIC COMPOUNDS |
US9650375B2 (en) | 2013-03-14 | 2017-05-16 | Merck Sharp & Dohme Corp. | Indole derivatives useful as anti-diabetic agents |
WO2014151206A1 (en) | 2013-03-15 | 2014-09-25 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase and their uses |
CA2905435A1 (en) | 2013-03-15 | 2014-09-25 | Synergy Pharmaceuticals Inc. | Compositions useful for the treatment of gastrointestinal disorders |
EP2781217A1 (en) | 2013-03-18 | 2014-09-24 | ETH Zurich | ROR gamma modulators |
EP3004138B1 (en) | 2013-06-05 | 2024-03-13 | Bausch Health Ireland Limited | Ultra-pure agonists of guanylate cyclase c, method of making and using same |
WO2015051496A1 (en) | 2013-10-08 | 2015-04-16 | Merck Sharp & Dohme Corp. | Antidiabetic tricyclic compounds |
AU2015308350B2 (en) | 2014-08-29 | 2020-03-05 | Tes Pharma S.R.L. | Inhibitors of alpha-amino-beta-carboxymuconic acid semialdehyde decarboxylase |
CN105198809A (zh) * | 2015-09-24 | 2015-12-30 | 绍兴文理学院 | 一种2-(1-酰亚胺基甲基)-1,2,3,4-四氢异喹啉衍生物及其合成方法与应用 |
CN105418498A (zh) * | 2015-12-30 | 2016-03-23 | 绍兴文理学院 | 一种1,2,3,4-四氢异喹啉衍生物及其合成方法与应用 |
WO2017194548A1 (en) | 2016-05-10 | 2017-11-16 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods and pharmaceutical compositions for the treatment of autoimmune inflammatory diseases |
WO2018069532A1 (en) | 2016-10-14 | 2018-04-19 | Tes Pharma S.R.L. | Inhibitors of alpha-amino-beta-carboxymuconic acid semialdehyde decarboxylase |
EP3551176A4 (en) | 2016-12-06 | 2020-06-24 | Merck Sharp & Dohme Corp. | ANTIDIABETIC HETEROCYCLIC COMPOUNDS |
EP3558298A4 (en) | 2016-12-20 | 2020-08-05 | Merck Sharp & Dohme Corp. | ANTIDIABETIC SPIROCHROMAN COMPOUNDS |
CN113302189A (zh) | 2018-11-20 | 2021-08-24 | Tes制药有限责任公司 | α-氨基-β-羧基己二烯二酸半醛去羧酶的抑制剂 |
CN112538100B (zh) * | 2020-12-16 | 2022-06-24 | 河南中医药大学 | 一种从黄柏中提取的具有抗炎活性的异喹啉生物碱苷类化合物及其制备方法与应用 |
WO2023164596A1 (en) * | 2022-02-25 | 2023-08-31 | The Katholieke Universiteit Leuven | Dihydroquinazolinones and related analogs for inhibiting yap/taz-tead |
Family Cites Families (24)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE204917C (ja) | ||||
DE258817C (ja) | ||||
CA205079A (en) * | 1920-10-26 | Nelson Lionel | Gas producer | |
DE261158C (ja) | ||||
CA110459A (en) * | 1907-12-09 | 1908-02-25 | Charles Albert Keller | Electric furnace |
CA173523A (en) * | 1916-04-01 | 1916-11-28 | Raymond B. Price | Textile material |
CA170679A (en) * | 1916-05-26 | 1916-07-11 | Edwin W. Webb | Car brake |
US3480714A (en) * | 1966-02-07 | 1969-11-25 | Ciba Geigy Corp | N-substituted isoquinolines as antiprotozoal agents |
DD204917A1 (de) * | 1981-12-31 | 1983-12-14 | Gerhard Kempter | Verfahren zur herstellung phenylsubstituierter und benzkondensierter cycloalkylaminoacetanilide |
JPS6153268A (ja) * | 1984-08-24 | 1986-03-17 | Hokuriku Seiyaku Co Ltd | アントラニルアミド誘導体 |
DD261158A1 (de) * | 1987-01-08 | 1988-10-19 | Univ Halle Wittenberg | Verfahren zur herstellung von 2-aminoalkyl-3,4-dihydro-4-oxo-7h-pyrrolo 2.3-d pyrimidinen |
DD258817A1 (de) * | 1987-01-19 | 1988-08-03 | Univ Halle Wittenberg | Verfahren zur herstellung von 2-(aminoalkyl) -pyrimido-4,5'-5,4 pyrrolo 3,2-f 1,4 thiazepinderivaten |
EP0494623A1 (en) * | 1991-01-11 | 1992-07-15 | Laboratoires Glaxo Sa | Acridine derivatives |
NZ268587A (en) * | 1993-06-22 | 1998-01-26 | Knoll Ag | 1-cycloalkyl substituted tetrahydroisoquinoline derivatives and pharmaceutical compositions |
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 |
AU716151B2 (en) * | 1996-11-27 | 2000-02-17 | Pfizer Inc. | 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 |
EP1075478B1 (en) * | 1998-05-08 | 2003-04-16 | 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 |
JP2003503480A (ja) * | 1999-07-06 | 2003-01-28 | バーテックス ファーマシューティカルズ インコーポレイテッド | ニューロン活性を有するn−ヘテロ環誘導体 |
-
2001
- 2001-03-12 JP JP2001567703A patent/JP4009460B2/ja not_active Expired - Lifetime
- 2001-03-12 WO PCT/EP2001/002733 patent/WO2001068609A1/en active IP Right Grant
- 2001-03-12 NZ NZ520624A patent/NZ520624A/xx not_active IP Right Cessation
- 2001-03-12 IL IL15098601A patent/IL150986A0/xx active IP Right Grant
- 2001-03-12 KR KR1020077016214A patent/KR20070087103A/ko active Search and Examination
- 2001-03-12 PT PT01933685T patent/PT1274687E/pt unknown
- 2001-03-12 MX MXPA02008797A patent/MXPA02008797A/es active IP Right Grant
- 2001-03-12 HU HU0300207A patent/HU227811B1/hu unknown
- 2001-03-12 AT AT01933685T patent/ATE286500T1/de active
- 2001-03-12 DE DE60108236T patent/DE60108236T2/de not_active Expired - Lifetime
- 2001-03-12 CN CNB018063268A patent/CN100393703C/zh not_active Expired - Lifetime
- 2001-03-12 CA CA002402431A patent/CA2402431C/en not_active Expired - Lifetime
- 2001-03-12 US US10/239,693 patent/US6703392B2/en not_active Expired - Lifetime
- 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 BR BRPI0109200A patent/BRPI0109200B8/pt not_active IP Right Cessation
- 2001-03-12 ES ES01933685T patent/ES2234840T3/es not_active Expired - Lifetime
- 2001-03-12 AU AU2001260113A patent/AU2001260113B2/en not_active Expired
-
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
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP2003527374A5 (ja) | ||
TW201336815A (zh) | (s)-1-(3-乙氧基-4-甲氧基苯基)-2-甲烷磺醯基乙胺之製備方法 | |
JP4515933B2 (ja) | 1,3,4,5−テトラヒドロ−2h−3−ベンゾアゼピン−2−オン化合物の新規な合成方法、並びにイバブラジン及び薬学的に許容され得る酸とのその付加塩の合成への適用 | |
JPH066565B2 (ja) | 光学活性なベンゼンスルホンアミド誘導体の製造法 | |
WO2007013698A1 (ja) | アルジミンまたはその誘導体を用いる一置換アルキル化化合物の製造方法 | |
HRP930508A2 (en) | Difenilpropilamina process for the preparation of the novel enylpropylamine derivatives | |
CA2794684A1 (en) | Process for preparing benzoxaboroles | |
WO2003097632A1 (fr) | Derives de propanolamine, procede de preparation de 3-n-methylamino-1-(2-thienyl)-1-propanols et procede de preparation de derives de propanolamine | |
CN114605275B (zh) | 一种无溴盐酸多巴胺合成方法 | |
WO2008077560A1 (en) | Process for the preparation of optically active 2-amino-1-phenylethanols | |
JP2013100367A (ja) | ジヒドロイソキノリンからのヘキサヒドロイソキノリンの調製 | |
KR101579991B1 (ko) | 거울상이성질성의 삼치환된 3,4-디하이드로-이소퀴놀린 유도체의 제조 공정 | |
CN101309903B (zh) | 制备thoc的新方法 | |
EP2227455B1 (en) | Trisubstituted 3,4-dihydro-1h-isoquinolin compound, process for its preparation, and its use | |
LT4928B (lt) | (1r,2s,4r)-(-)-2-[(2'-{n,n-dimetilamino}-etoksi)]-2-fenil-1,7,7-trimetil-biciklo[2.2.1]heptano ir jo farmaciškai priimtinų adityvinių druskų su rūgštimis gavimo būdas | |
US6635773B2 (en) | Process for preparing citalopram | |
CN102276608A (zh) | 一种四氢-β-咔啉二酮哌嗪类化合物的合成方法 | |
CN110684043B (zh) | 一种c-n轴手性芳胺化合物及其制备方法 | |
JP2004516290A (ja) | 新規プロセス | |
US10428098B2 (en) | Processes for preparing and using ruthenium and osmium complexes | |
JPWO2007074553A1 (ja) | 立体選択的にストレッカー反応を進行させ得る触媒、およびそれを用いたα−アミノニトリル誘導体を立体選択的に製造するための方法 | |
WO2022262143A1 (zh) | 一种吡啶硼酸酯的制备方法 | |
CN117756622A (zh) | 一种沙库巴曲关键中间体的制备方法 | |
Kim et al. | Alkylation of N′-[(S)-1′-Phenylethyl]-N-(diphenylmethylene) glycinamide using a Phase Transfer Catalyst (PTC) for Practical Asymmetric Syntheses of α-Amino Acid Derivatives | |
CN107513015A (zh) | 一种依那普利中间体合成母液制备3‑苯甲酰基丙烯酸乙酯的方法 |