JP2005501841A5 - - Google Patents
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- JP2005501841A5 JP2005501841A5 JP2003519057A JP2003519057A JP2005501841A5 JP 2005501841 A5 JP2005501841 A5 JP 2005501841A5 JP 2003519057 A JP2003519057 A JP 2003519057A JP 2003519057 A JP2003519057 A JP 2003519057A JP 2005501841 A5 JP2005501841 A5 JP 2005501841A5
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- JP
- Japan
- Prior art keywords
- formula
- compound
- acid
- group
- alkyl
- 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.)
- Ceased
Links
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 239000007848 Bronsted acid Substances 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 3
- 229910010082 LiAlH Inorganic materials 0.000 claims description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- 229920000137 polyphosphoric acid Polymers 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- 125000004429 atom Chemical group 0.000 claims 3
- 229910052740 iodine Inorganic materials 0.000 claims 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 229910052794 bromium Inorganic materials 0.000 claims 2
- 239000003638 chemical reducing agent Substances 0.000 claims 2
- 239000000460 chlorine Substances 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- -1 heterocyclic pentalene derivative Chemical class 0.000 claims 2
- 239000011630 iodine Substances 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 230000000737 periodic effect Effects 0.000 claims 2
- 229910052698 phosphorus Inorganic materials 0.000 claims 2
- 229910052710 silicon Inorganic materials 0.000 claims 2
- 125000004434 sulfur atom Chemical group 0.000 claims 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 239000012024 dehydrating agents Substances 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-N methyl sulfate Chemical compound COS(O)(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-N 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 229920002554 vinyl polymer Polymers 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 0 *C(C1[*+])C(C(*)=C(*)*2)=C2C1=O Chemical compound *C(C1[*+])C(C(*)=C(*)*2)=C2C1=O 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- ICHPKWCNDGFKTI-UHFFFAOYSA-N 3-(4-chlorophenyl)-2,5-dimethyl-4,5-dihydrocyclopenta[b]thiophen-6-one Chemical compound O=C1C(C)CC2=C1SC(C)=C2C1=CC=C(Cl)C=C1 ICHPKWCNDGFKTI-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP01202930 | 2001-08-01 | ||
| PCT/EP2002/007680 WO2003014107A1 (en) | 2001-08-01 | 2002-07-10 | Process for the preparation of heterocyclic pentalene derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2005501841A JP2005501841A (ja) | 2005-01-20 |
| JP2005501841A5 true JP2005501841A5 (enExample) | 2006-01-05 |
Family
ID=8180742
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003519057A Ceased JP2005501841A (ja) | 2001-08-01 | 2002-07-10 | 複素環式ペンタレン誘導体の製造方法 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US6930190B2 (enExample) |
| EP (1) | EP1412347B1 (enExample) |
| JP (1) | JP2005501841A (enExample) |
| AT (1) | ATE315559T1 (enExample) |
| DE (1) | DE60208683T2 (enExample) |
| WO (1) | WO2003014107A1 (enExample) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4332029B2 (ja) | 2001-06-12 | 2009-09-16 | バーゼル・ポリオレフィン・ゲーエムベーハー | １−ブテンの重合方法 |
| WO2003025028A1 (de) * | 2001-09-14 | 2003-03-27 | Basell Polyolefine Gmbh | Verfahren zur polymerisation von olefinen |
| DE10145453A1 (de) * | 2001-09-14 | 2003-06-05 | Basell Polyolefine Gmbh | Monocyclopentadienylkomplexe mit einem kondensierten Heterocyclus |
| EP1448578B1 (en) | 2001-11-30 | 2006-07-26 | Basell Polyolefine GmbH | Metallocene compounds and process for the preparation of propylene polymers |
| ATE445651T1 (de) | 2002-09-06 | 2009-10-15 | Basell Polyolefine Gmbh | Verfahren zur copolymerisation von ethylen |
| WO2004033510A2 (en) | 2002-10-10 | 2004-04-22 | Basell Polyolefine Gmbh | Process for the copolymerization of ethylene |
| DE10260095A1 (de) * | 2002-12-19 | 2004-07-01 | Basell Polyolefine Gmbh | Verfahren zur Herstellung von heterocyclischen Ketonen |
| AU2004280559A1 (en) * | 2003-09-19 | 2005-04-21 | Sri International | Methods and apparatuses for producing metallic compositions via reduction of metal halides |
| FR2860792B1 (fr) * | 2003-10-10 | 2006-02-24 | Sanofi Synthelabo | Derives de thiophene-2-carboxamide, leur preparation et leur application en therapeutique |
| WO2006005648A1 (en) | 2004-07-13 | 2006-01-19 | Basell Polyolefine Gmbh | Metallocene compounds, ligands used in their preparation, preparation of 1-butene polymers and 1-butene polymers therefrom |
| DE602005005334T2 (de) | 2004-07-22 | 2009-03-26 | Basell Polyolefine Gmbh | 1-butenpolymerzusammensetzung |
| BRPI0513108A (pt) | 2004-07-22 | 2008-04-29 | Basell Polyolefine Gmbh | processo para produzir polìmeros de buteno-1 fracionáveis |
| WO2006010379A1 (en) | 2004-07-29 | 2006-02-02 | Actelion Pharmaceuticals Ltd. | Novel thiophene derivatives as immunosuppressive agents |
| KR101229293B1 (ko) | 2004-10-18 | 2013-02-05 | 바셀 폴리올레핀 이탈리아 에스.알.엘 | 이소탁틱도가 낮은 부텐-1 (공)중합체 |
| KR101216434B1 (ko) | 2004-10-21 | 2012-12-28 | 바젤 폴리올레핀 게엠베하 | 1-부텐 중합체 및 그 제조 방법 |
| US8051611B2 (en) * | 2005-06-24 | 2011-11-08 | Dryvit Systems, Inc. | Exterior insulation and finish system and method and tool for installing same |
| RU2008101805A (ru) | 2005-06-24 | 2009-07-27 | Актелион Фармасьютиклз Лтд (Ch) | Новые производные тиофена |
| DE102005061326A1 (de) * | 2005-12-20 | 2007-06-21 | Basell Polyolefine Gmbh | Verfahren zur Herstellung von Metallocenen aus recycelten, substituierten Cyclopentadienylderivaten |
| JP5063615B2 (ja) | 2006-01-24 | 2012-10-31 | アクテリオン ファーマシューティカルズ リミテッド | 新規ピリジン誘導体 |
| US8097682B2 (en) * | 2006-08-30 | 2012-01-17 | Basell Polyolefine Gmbh | 1-butene propylene copolymer compositions |
| EP2057227B1 (en) * | 2006-08-30 | 2009-12-09 | Basell Polyolefine GmbH | 1-butene propylene copolymer compositions |
| DE102008015033A1 (de) | 2008-03-17 | 2009-09-24 | Aicuris Gmbh & Co. Kg | Substituierte (Pyrazolyl-carbonyl)imidazolidinone und ihre Verwendung |
| DE102008015032A1 (de) | 2008-03-17 | 2009-09-24 | Aicuris Gmbh & Co. Kg | Substituierte Pyrazolamide und ihre Verwendung |
| JP2011515516A (ja) * | 2008-03-20 | 2011-05-19 | バーゼル・ポリオレフィン・イタリア・ソチエタ・ア・レスポンサビリタ・リミタータ | １−ブテンコポリマー |
| JP2011515518A (ja) * | 2008-03-20 | 2011-05-19 | バーゼル・ポリオレフィン・イタリア・ソチエタ・ア・レスポンサビリタ・リミタータ | １−ブテン系ポリマー類の組成物類 |
| KR20100133987A (ko) * | 2008-03-20 | 2010-12-22 | 바셀 폴리올레핀 이탈리아 에스.알.엘 | 1-부텐 삼원중합체 |
| KR20100127226A (ko) * | 2008-03-20 | 2010-12-03 | 바셀 폴리올레핀 이탈리아 에스.알.엘 | 1-부텐 공중합체 |
| DE102008062863A1 (de) | 2008-12-17 | 2010-06-24 | Aicuris Gmbh & Co. Kg | Substituierte (Thiophenyl-carbonyl)imidazolidinone und ihre Verwendung |
| DE102008062878A1 (de) | 2008-12-17 | 2010-06-24 | Aicuris Gmbh & Co. Kg | Substituierte Furancarboxamide und ihre Verwendung |
| CN110372662B (zh) * | 2019-08-07 | 2021-12-21 | 西安近代化学研究所 | 基于环戊烷并噻吩骨架的液晶化合物及其合成方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4496742A (en) * | 1981-10-13 | 1985-01-29 | The Upjohn Company | Analogs of 5,6-dihydro PGI2 |
| DE3147714A1 (de) * | 1981-11-27 | 1983-06-01 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | Neue prostacycline und verfahren zu ihrer herstellung |
| JPS63122669A (ja) * | 1986-10-25 | 1988-05-26 | メルク・パテント・ゲゼルシヤフト・ミツト・ベシユレンクテル・ハフツング | 複素環状液晶化合物 |
| CA1333612C (en) * | 1988-09-23 | 1994-12-20 | Paul Howard Briner | Process for the preparation of cyclopentene, cyclopentane, and cyclohexane derivatives |
| IL103106A (en) * | 1991-09-25 | 1998-06-15 | Sanofi Elf | Ethers of thienocyclopentanone oximes, their preparation and pharmaceutical compositions containing them |
| EP0789022B1 (en) * | 1994-02-17 | 2003-06-18 | Asahi Glass Company Ltd. | Difluoroprostacyclins, intermediates for production thereof and processes for production thereof |
| FR2773798B1 (fr) * | 1998-01-16 | 2001-02-02 | Adir | Nouveaux composes tricycliques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| US6057316A (en) * | 1998-05-12 | 2000-05-02 | American Home Products Corporation | 4-aryl-1-oxa-9-thia-cyclopenta[b]fluorenes |
| US6762316B1 (en) * | 1999-06-28 | 2004-07-13 | Biocryst Pharmaceuticals, Inc. | Preparation of substituted cyclopentane and cyclopentene compounds and certain intermediates |
| US6444833B1 (en) | 1999-12-15 | 2002-09-03 | Basell Technology Company Bv | Metallocene compounds, process for their preparation and their use in catalytic systems for the polymerization of olefins |
-
2002
- 2002-07-10 EP EP02748851A patent/EP1412347B1/en not_active Expired - Lifetime
- 2002-07-10 AT AT02748851T patent/ATE315559T1/de not_active IP Right Cessation
- 2002-07-10 WO PCT/EP2002/007680 patent/WO2003014107A1/en not_active Ceased
- 2002-07-10 JP JP2003519057A patent/JP2005501841A/ja not_active Ceased
- 2002-07-10 DE DE60208683T patent/DE60208683T2/de not_active Expired - Lifetime
- 2002-07-10 US US10/485,497 patent/US6930190B2/en not_active Expired - Fee Related
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