NO323016B1 - Fremgangsmate for fremstilling av substituerte antrakinoner - Google Patents
Fremgangsmate for fremstilling av substituerte antrakinoner Download PDFInfo
- Publication number
- NO323016B1 NO323016B1 NO19984625A NO984625A NO323016B1 NO 323016 B1 NO323016 B1 NO 323016B1 NO 19984625 A NO19984625 A NO 19984625A NO 984625 A NO984625 A NO 984625A NO 323016 B1 NO323016 B1 NO 323016B1
- Authority
- NO
- Norway
- Prior art keywords
- group
- carbon atoms
- hydrogen atom
- general formula
- linear
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 25
- 150000004056 anthraquinones Chemical class 0.000 title claims abstract description 14
- 238000002360 preparation method Methods 0.000 title claims abstract description 14
- 239000003810 Jones reagent Substances 0.000 claims abstract description 15
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 claims abstract description 13
- 238000005698 Diels-Alder reaction Methods 0.000 claims abstract description 10
- -1 acyclic diene Chemical class 0.000 claims abstract description 9
- 238000010511 deprotection reaction Methods 0.000 claims abstract description 7
- 230000001590 oxidative effect Effects 0.000 claims abstract description 7
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 claims abstract description 6
- KQPYUDDGWXQXHS-UHFFFAOYSA-N juglone Chemical compound O=C1C=CC(=O)C2=C1C=CC=C2O KQPYUDDGWXQXHS-UHFFFAOYSA-N 0.000 claims description 22
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- VYTBDSUNRJYVHL-UHFFFAOYSA-N beta-Hydrojuglone Natural products O=C1CCC(=O)C2=C1C=CC=C2O VYTBDSUNRJYVHL-UHFFFAOYSA-N 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- OTBHDFWQZHPNPU-UHFFFAOYSA-N 1,2,3,4-tetrahydroanthracene-9,10-dione Chemical class O=C1C2=CC=CC=C2C(=O)C2=C1CCCC2 OTBHDFWQZHPNPU-UHFFFAOYSA-N 0.000 claims description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 6
- 229930192627 Naphthoquinone Natural products 0.000 claims description 6
- 150000002791 naphthoquinones Chemical class 0.000 claims description 6
- KMUONIBRACKNSN-UHFFFAOYSA-N potassium dichromate Chemical compound [K+].[K+].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O KMUONIBRACKNSN-UHFFFAOYSA-N 0.000 claims description 6
- TXBMCLDHFRIQLA-UHFFFAOYSA-N trimethyl(3-methylbuta-1,3-dienoxy)silane Chemical compound CC(=C)C=CO[Si](C)(C)C TXBMCLDHFRIQLA-UHFFFAOYSA-N 0.000 claims description 6
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 6
- 239000002841 Lewis acid Substances 0.000 claims description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 5
- 150000007517 lewis acids Chemical class 0.000 claims description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000004423 acyloxy group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 4
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 4
- 230000003197 catalytic effect Effects 0.000 claims description 3
- 229910052801 chlorine Chemical group 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 150000001993 dienes Chemical class 0.000 claims description 3
- 235000005074 zinc chloride Nutrition 0.000 claims description 3
- 239000011592 zinc chloride Substances 0.000 claims description 3
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims description 2
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 2
- KWZWNVAHEQHCTQ-UHFFFAOYSA-N diacetyloxyboranyl acetate Chemical compound CC(=O)OB(OC(C)=O)OC(C)=O KWZWNVAHEQHCTQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 239000003814 drug Substances 0.000 abstract 1
- LQGUBLBATBMXHT-UHFFFAOYSA-N chrysophanol Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC(O)=C3C(=O)C2=C1O LQGUBLBATBMXHT-UHFFFAOYSA-N 0.000 description 30
- NZPQWZZXRKZCDU-UHFFFAOYSA-N chrysophanol Natural products Cc1cc(O)c2C(=O)c3c(O)cccc3Oc2c1 NZPQWZZXRKZCDU-UHFFFAOYSA-N 0.000 description 15
- OGURMTXRUQGVMS-UHFFFAOYSA-N 1,8-dihydroxy-2-methylanthracene-9,10-dione Chemical compound C1=CC(O)=C2C(=O)C3=C(O)C(C)=CC=C3C(=O)C2=C1 OGURMTXRUQGVMS-UHFFFAOYSA-N 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 229940076442 9,10-anthraquinone Drugs 0.000 description 5
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- AFHWNNJNTNLCQF-UHFFFAOYSA-N pachybasin Natural products C1=CC=C2C(=O)C3=CC(C)=CC(O)=C3C(=O)C2=C1 AFHWNNJNTNLCQF-UHFFFAOYSA-N 0.000 description 4
- LEHBURLTIWGHEM-UHFFFAOYSA-N pyridinium chlorochromate Chemical compound [O-][Cr](Cl)(=O)=O.C1=CC=[NH+]C=C1 LEHBURLTIWGHEM-UHFFFAOYSA-N 0.000 description 4
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000004809 thin layer chromatography Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000005899 aromatization reaction Methods 0.000 description 3
- 150000001844 chromium Chemical class 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000007800 oxidant agent Substances 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 230000007306 turnover Effects 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- 150000000191 1,4-naphthoquinones Chemical class 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical class C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- 238000006117 Diels-Alder cycloaddition reaction Methods 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 238000007259 addition reaction Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- UQGOYQLRRBTVFM-UHFFFAOYSA-N buta-1,3-dienoxy(trimethyl)silane Chemical compound C[Si](C)(C)OC=CC=C UQGOYQLRRBTVFM-UHFFFAOYSA-N 0.000 description 2
- QBPFLULOKWLNNW-UHFFFAOYSA-N chrysazin Chemical compound O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O QBPFLULOKWLNNW-UHFFFAOYSA-N 0.000 description 2
- 238000005828 desilylation reaction Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 229910001923 silver oxide Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- BOKGTLAJQHTOKE-UHFFFAOYSA-N 1,5-dihydroxynaphthalene Chemical compound C1=CC=C2C(O)=CC=CC2=C1O BOKGTLAJQHTOKE-UHFFFAOYSA-N 0.000 description 1
- JPUMBKSFAHUWOU-UHFFFAOYSA-N 6-methoxy-4-methylpyran-2-one Chemical compound COC1=CC(C)=CC(=O)O1 JPUMBKSFAHUWOU-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- JPICKYUTICNNNJ-UHFFFAOYSA-N anthrarufin Chemical compound O=C1C2=C(O)C=CC=C2C(=O)C2=C1C=CC=C2O JPICKYUTICNNNJ-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 229910000423 chromium oxide Inorganic materials 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000017858 demethylation Effects 0.000 description 1
- 238000010520 demethylation reaction Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C46/00—Preparation of quinones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C46/00—Preparation of quinones
- C07C46/02—Preparation of quinones by oxidation giving rise to quinoid structures
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C50/00—Quinones
- C07C50/26—Quinones containing groups having oxygen atoms singly bound to carbon atoms
- C07C50/34—Quinones containing groups having oxygen atoms singly bound to carbon atoms the quinoid structure being part of a condensed ring system having three rings
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9701161A FR2759079B1 (fr) | 1997-02-03 | 1997-02-03 | Procede de preparation d'anthraquinones substituees et application a la preparation de rheines |
| PCT/FR1998/000189 WO1998033757A1 (fr) | 1997-02-03 | 1998-02-02 | Procede de preparation d'anthraquinones substituees, et application a la preparation de rheines |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO984625L NO984625L (no) | 1998-10-02 |
| NO984625D0 NO984625D0 (no) | 1998-10-02 |
| NO323016B1 true NO323016B1 (no) | 2006-12-27 |
Family
ID=9503239
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19984625A NO323016B1 (no) | 1997-02-03 | 1998-10-02 | Fremgangsmate for fremstilling av substituerte antrakinoner |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US6057461A (cs) |
| EP (1) | EP0909268B1 (cs) |
| JP (1) | JP4083232B2 (cs) |
| KR (1) | KR100562763B1 (cs) |
| CN (1) | CN1106375C (cs) |
| AT (1) | ATE218528T1 (cs) |
| AU (1) | AU729548B2 (cs) |
| BR (1) | BR9805966A (cs) |
| CA (1) | CA2251024A1 (cs) |
| CZ (1) | CZ294186B6 (cs) |
| DE (1) | DE69805729T2 (cs) |
| DK (1) | DK0909268T3 (cs) |
| ES (1) | ES2176967T3 (cs) |
| FR (1) | FR2759079B1 (cs) |
| HU (1) | HUP0001654A3 (cs) |
| IL (1) | IL126198A0 (cs) |
| NO (1) | NO323016B1 (cs) |
| NZ (1) | NZ332138A (cs) |
| PL (1) | PL190145B1 (cs) |
| PT (1) | PT909268E (cs) |
| RU (1) | RU2202535C2 (cs) |
| SI (1) | SI0909268T1 (cs) |
| SK (1) | SK282696B6 (cs) |
| TR (1) | TR199801978T1 (cs) |
| WO (1) | WO1998033757A1 (cs) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19936282A1 (de) * | 1999-08-02 | 2001-02-08 | Bayer Ag | Verfahren zur Herstellung von Arylaminohydroxyanthrachinonen |
| DE10038101A1 (de) * | 2000-08-04 | 2002-02-14 | Degussa | Verfahren zur Herstellung von 2-(4-Methyl-3-pentenyl)-anthrachinon |
| EP1666446A1 (en) * | 2004-11-12 | 2006-06-07 | Laboratoire Medidom S.A. | Process for preparing rhein and diacerein |
| CN107698434A (zh) * | 2016-08-09 | 2018-02-16 | 常州高新技术产业开发区三维工业技术研究所有限公司 | 一种大黄酸的合成工艺 |
| CN107619803B (zh) * | 2017-09-19 | 2020-03-03 | 浙江大学 | 一种暗黄链霉酸和暗黄链霉酮的制备及其医药用途 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| LU61653A1 (cs) * | 1970-09-07 | 1972-06-27 | ||
| SU614086A1 (ru) * | 1976-07-19 | 1978-07-05 | Рубежанский филиал Ворошиловградского машиностроительного института | Способ получени антрахинона |
| DE3305528A1 (de) * | 1983-02-18 | 1984-08-23 | Rütgerswerke AG, 6000 Frankfurt | Verfahren zur herstellung von phenanthrenchinon |
| JPS62126170A (ja) * | 1985-11-28 | 1987-06-08 | Mitsui Toatsu Chem Inc | ４−（４−ピリジル）シクロヘキサノンを製造する方法 |
| GB2190080B (en) * | 1986-05-02 | 1990-03-21 | Koppers Co Inc | Anthraquinones |
| FR2740772B1 (fr) * | 1995-11-02 | 1998-01-16 | Girex | Procede de preparation d'anthraquinones substituees et application a la preparation de rheines |
| KR0182834B1 (ko) * | 1996-05-16 | 1999-05-15 | 김흥기 | 안트라퀴논류의 제조방법 |
-
1997
- 1997-02-03 FR FR9701161A patent/FR2759079B1/fr not_active Expired - Fee Related
-
1998
- 1998-02-02 CN CN98800081A patent/CN1106375C/zh not_active Expired - Fee Related
- 1998-02-02 WO PCT/FR1998/000189 patent/WO1998033757A1/fr active IP Right Grant
- 1998-02-02 PL PL98329129A patent/PL190145B1/pl not_active IP Right Cessation
- 1998-02-02 IL IL12619898A patent/IL126198A0/xx not_active IP Right Cessation
- 1998-02-02 HU HU0001654A patent/HUP0001654A3/hu unknown
- 1998-02-02 KR KR1019980707883A patent/KR100562763B1/ko not_active Expired - Fee Related
- 1998-02-02 BR BR9805966-1A patent/BR9805966A/pt not_active Application Discontinuation
- 1998-02-02 TR TR1998/01978T patent/TR199801978T1/xx unknown
- 1998-02-02 RU RU98120157/04A patent/RU2202535C2/ru not_active IP Right Cessation
- 1998-02-02 DE DE69805729T patent/DE69805729T2/de not_active Expired - Fee Related
- 1998-02-02 PT PT98905479T patent/PT909268E/pt unknown
- 1998-02-02 AT AT98905479T patent/ATE218528T1/de not_active IP Right Cessation
- 1998-02-02 EP EP98905479A patent/EP0909268B1/fr not_active Expired - Lifetime
- 1998-02-02 JP JP53259898A patent/JP4083232B2/ja not_active Expired - Fee Related
- 1998-02-02 ES ES98905479T patent/ES2176967T3/es not_active Expired - Lifetime
- 1998-02-02 AU AU61051/98A patent/AU729548B2/en not_active Ceased
- 1998-02-02 US US09/155,643 patent/US6057461A/en not_active Expired - Fee Related
- 1998-02-02 SK SK1341-98A patent/SK282696B6/sk unknown
- 1998-02-02 NZ NZ332138A patent/NZ332138A/xx unknown
- 1998-02-02 CZ CZ19982924A patent/CZ294186B6/cs not_active IP Right Cessation
- 1998-02-02 SI SI9830228T patent/SI0909268T1/xx unknown
- 1998-02-02 CA CA002251024A patent/CA2251024A1/fr not_active Abandoned
- 1998-02-02 DK DK98905479T patent/DK0909268T3/da active
- 1998-10-02 NO NO19984625A patent/NO323016B1/no unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Mckillop et al. | Organic synthesis using supported reagents-Part II | |
| Nongkunsarn et al. | Oxidative rearrangement of imines to formamides using sodium perborate | |
| Engman et al. | Organotellurium chemistry. 7. Reductive removal of electronegative. alpha.-substituents of ketones and acids by a tellurolate reagent | |
| NO323016B1 (no) | Fremgangsmate for fremstilling av substituerte antrakinoner | |
| AU8998198A (en) | Method for manufacturing 3,4-dihydroxy-3-cyclobutene-1,2- dione | |
| Aranda et al. | Chirality of nucleophilic reactions of axial aldehydes and methyl ketones in the diterpene series | |
| US5235091A (en) | Process for preparing diphenylmethane compounds | |
| US5948924A (en) | Process for the preparation of substituted anthraquinones and application in the preparation of rheins | |
| Cambie et al. | Chemistry of the Podocarpaceae. LXIII. Ring-C oxidation of totarol | |
| Yamamoto et al. | A convenient synthesis of 4-and 5-acetyltropolone. | |
| Fleming et al. | Reactions of phenyldimethylsilyllithium with β-N, N-dimethylaminoenones: A convenient synthesis of β-dimethyl (phenyl) silylacrylic acid and its derivatives | |
| AU2003231149B2 (en) | Selective oxidation process with enhanced safety | |
| D'Haenens et al. | On the Synthesis and Conformational Aspects of 2‐methyl and 2‐t. Butyl Substituted 1, 3‐Cyclopentane and Cyclohexane Diols | |
| US4900858A (en) | Process for the preparation of a 6-halo-3-methyl-1-trialkylsilyloxy-1,3,5-hexatriene | |
| Nickon et al. | A solvolysis route to a macrobicyclic allene | |
| JP3367057B2 (ja) | ４ーｔーブチルジオキシー２，５ーシクロヘキサジエンー１ーオン類の製造法 | |
| EP0098012B1 (en) | Process for preparing (o-hydroxyaryl)-methanols | |
| US4861917A (en) | Process for preparing macrocyclic 2-halogenoketones | |
| MATOBA et al. | Chemistry of 2-Methoxy-2, 5-cyclohexadienone. V. Photochemical Rearrangement and Oxidation of 2-Methoxy-4-methyl-4-phenyl-2-cyclohexenone and 2-Methoxy-4-methyl-4-phenyl-2, 5-cyclohexadienone | |
| JP2943363B2 (ja) | フェニルケトン類の製造法 | |
| CA1257297A (en) | Process for preparing substituted benzotrichlorides | |
| Cagle | Synthesis and Nuclear Magnetic Resonance Spectroscopic Investigation of Crowded Anisoles� | |
| Abdul-Majid | Some Aspects of Carbon-Nitrogen Double Bond Photochemistry | |
| WO1989004819A1 (fr) | Derives de trifluoromethyl-1-tetralines, leur preparation et leur application pour la synthese de composes presentant des proprietes therapeutiques | |
| JPH07121888B2 (ja) | ｏ−ジヒドロキシル化芳香族化合物の製造方法 |