JP2002526544A5 - - Google Patents
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- Publication number
- JP2002526544A5 JP2002526544A5 JP2000574532A JP2000574532A JP2002526544A5 JP 2002526544 A5 JP2002526544 A5 JP 2002526544A5 JP 2000574532 A JP2000574532 A JP 2000574532A JP 2000574532 A JP2000574532 A JP 2000574532A JP 2002526544 A5 JP2002526544 A5 JP 2002526544A5
- Authority
- JP
- Japan
- Prior art keywords
- reduced pressure
- under reduced
- solvent
- mmol
- water
- 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
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- 239000002904 solvent Substances 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 239000007787 solid Substances 0.000 description 12
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 239000011521 glass Substances 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 229960003512 nicotinic acid Drugs 0.000 description 5
- 235000001968 nicotinic acid Nutrition 0.000 description 5
- 239000011664 nicotinic acid Substances 0.000 description 5
- KLDXJTOLSGUMSJ-BXKVDMCESA-N (3s,3as,6s,6as)-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3,6-diol Chemical compound O[C@H]1CO[C@H]2[C@@H](O)CO[C@H]21 KLDXJTOLSGUMSJ-BXKVDMCESA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- KLDXJTOLSGUMSJ-JGWLITMVSA-N Isosorbide Chemical compound O[C@@H]1CO[C@@H]2[C@@H](O)CO[C@@H]21 KLDXJTOLSGUMSJ-JGWLITMVSA-N 0.000 description 4
- 229960002479 isosorbide Drugs 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
- JYWNYMJKURVPFH-UHFFFAOYSA-N N-gamma-Acetyl-N-2-Formyl-5-Methoxykynurenamine Chemical compound COC1=CC=C(NC=O)C(C(=O)CCNC(C)=O)=C1 JYWNYMJKURVPFH-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 0 *[C@](CO[C@@]12)[C@]1OC[C@@]2O Chemical compound *[C@](CO[C@@]12)[C@]1OC[C@@]2O 0.000 description 2
- KHLBHKYZTXYEHP-UHFFFAOYSA-N 2-methylpyridine-3-carbothioyl chloride Chemical compound CC1=NC=CC=C1C(Cl)=S KHLBHKYZTXYEHP-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-ZSJDYOACSA-N Heavy water Chemical compound [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229960003827 isosorbide mononitrate Drugs 0.000 description 2
- YWXYYJSYQOXTPL-SLPGGIOYSA-N isosorbide mononitrate Chemical compound [O-][N+](=O)O[C@@H]1CO[C@@H]2[C@@H](O)CO[C@@H]21 YWXYYJSYQOXTPL-SLPGGIOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000004237 preparative chromatography Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 2
- JYWKEVKEKOTYEX-UHFFFAOYSA-N 2,6-dibromo-4-chloroiminocyclohexa-2,5-dien-1-one Chemical compound ClN=C1C=C(Br)C(=O)C(Br)=C1 JYWKEVKEKOTYEX-UHFFFAOYSA-N 0.000 description 1
- GOTPCIOLZMWNHT-UHFFFAOYSA-N 2-ethylpyridine-3-carbothioic s-acid Chemical compound CCC1=NC=CC=C1C(O)=S GOTPCIOLZMWNHT-UHFFFAOYSA-N 0.000 description 1
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 1
- OCEMBWMMHUSVMT-UHFFFAOYSA-N CSc(nccc1)c1C(Cl)=O Chemical compound CSc(nccc1)c1C(Cl)=O OCEMBWMMHUSVMT-UHFFFAOYSA-N 0.000 description 1
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000006345 epimerization reaction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- -1 for example Chemical compound 0.000 description 1
- 210000002196 fr. b Anatomy 0.000 description 1
- 210000003918 fraction a Anatomy 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 150000003566 thiocarboxylic acids Chemical class 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES009802076A ES2142773B1 (es) | 1998-10-07 | 1998-10-07 | Derivados de mononitrato de isosorbida y su empleo como agentes vasodilatadores con tolerancia desminuida. |
| ES9802076 | 1998-10-07 | ||
| PCT/ES1999/000316 WO2000020420A1 (es) | 1998-10-07 | 1999-10-04 | Derivados de mononitrato de isosorbida y su empleo como agentes vasodilatadores con tolerancia disminuida |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2002526544A JP2002526544A (ja) | 2002-08-20 |
| JP2002526544A5 true JP2002526544A5 (enExample) | 2006-10-19 |
| JP4659214B2 JP4659214B2 (ja) | 2011-03-30 |
Family
ID=8305360
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000574532A Expired - Fee Related JP4659214B2 (ja) | 1998-10-07 | 1999-10-04 | イソソルビドモノニトレートの誘導体及び耐性が低下した血管拡張剤としてのその使用 |
Country Status (40)
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2258365B1 (es) * | 2003-10-03 | 2007-12-01 | Lacer, S.A. | Derivados de disulfuro, sulfuro, sulfoxido y sulfona de azucares ciclicos y sus usos. |
| EP1941876A1 (en) * | 2006-12-28 | 2008-07-09 | Lacer, S.A. | Isosorbide mononitrate derivatives for the treatment of Inflammation and ocular hypertension |
| ES2332565B1 (es) * | 2007-01-23 | 2010-10-21 | Lacer, S.A. | Uso de derivados de mononitrato de dianhidrohexita como agentes antiinflamatorios. |
| IE20070934A1 (en) | 2007-12-21 | 2009-06-24 | Trinity College Dublin | Efficient aspirin prodrugs |
| EP2719700A1 (en) | 2008-01-09 | 2014-04-16 | Amura Therapeutics Limited | Tetrahydrofuro(3,2-b)pyrrol-3-one derivatives as inhibitors of cysteine proteinases |
| WO2009098113A1 (en) * | 2008-02-07 | 2009-08-13 | Nicox S.A. | Nitric oxide donor compounds |
| EP2149576A1 (en) | 2008-07-22 | 2010-02-03 | Lacer, S.A. | Isosorbide Nitrates having vasodilating activity |
| EP2149577B1 (en) * | 2008-07-22 | 2011-04-27 | Lacer, S.A. | New stereospecific method for the preparation of dioxa-bicyclooctane compounds |
| EP2177216A1 (en) | 2008-10-13 | 2010-04-21 | Lacer, S.A. | Use of dianhydrohexite mononitrate derivatives as healing agents |
| WO2010055138A1 (en) * | 2008-11-14 | 2010-05-20 | Lacer, S.A. | New stereospecific method for the preparation of dioxa-bicyclooctane compounds |
| EP2199294A1 (en) * | 2008-12-19 | 2010-06-23 | Lacer, S.A. | New stereospecific method for the preparation of dioxa bicyclooctane nitrate compounds |
| ES2423939T3 (es) * | 2009-09-10 | 2013-09-25 | Cognis Ip Management Gmbh | Derivados de isosorburo gliceril éter y su empleo en aplicaciones de uso doméstico |
| EP2515899B1 (en) * | 2009-12-23 | 2016-05-25 | ARCA biopharma, Inc. | Methods and compositions for cardiovascular diseases and conditions |
| CN102241687A (zh) * | 2011-05-23 | 2011-11-16 | 中国人民解放军第四军医大学 | 抗缺血/再灌注损伤的药物 |
| JP6158194B2 (ja) | 2011-10-24 | 2017-07-05 | ニコックス サイエンス アイルランド | キノン系一酸化窒素供与化合物 |
| HK1217323A1 (zh) * | 2013-03-05 | 2017-01-06 | 阿彻丹尼尔斯米德兰德公司 | 异己糖醇单三氟甲磺酸酯及其合成方法 |
| WO2014169976A1 (en) | 2013-04-18 | 2014-10-23 | Nicox Science Ireland | Quinone based nitric oxide donating compounds |
| CN104650108B (zh) * | 2013-11-18 | 2017-05-24 | 富力 | 连翘脂素硫酸酯及其衍生物、制备方法及其应用 |
| CN105461731B (zh) * | 2014-08-07 | 2017-05-24 | 富力 | 连翘脂素布洛芬酯、其制备及其应用 |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1356374A (fr) | 1963-02-12 | 1964-03-27 | Machine à fonctions multiples pour le travail du bois | |
| AU465217B2 (en) | 1971-04-29 | 1975-09-18 | American Home Products Corporation | Mononitrte esters of 1,4:3, 6-dianhydro-d-glucitol |
| US3886196A (en) | 1973-02-07 | 1975-05-27 | Phillips Petroleum Co | Magnesium-aluminum-silicate-phosphate catalysts for ammonialytic cleavage of lactams to form omega-aminonitriles |
| DE3028289C2 (de) | 1980-07-25 | 1986-11-27 | Dr. Willmar Schwabe GmbH & Co, 7500 Karlsruhe | 2-O- und 5-O-substituierte 1.4;3.6-Dianhydro-hexit-mononitrate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende pharmazeutische Zubereitungen |
| DE3248548A1 (de) | 1982-12-29 | 1984-07-05 | Heinrich Mack Nachf., 7918 Illertissen | Acylderivate von 1,4:3,6-dianhydro-hexiten, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
| DE3421072A1 (de) | 1984-06-06 | 1985-12-12 | Heinrich Mack Nachf., 7918 Illertissen | 1,4:3,6-dianhydro-hexit-derivate, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
| DE3602067A1 (de) | 1986-01-24 | 1987-07-30 | Mack Chem Pharm | 2,6-dioxabicyclo(3.3.0)octan-derivate, ihre herstellung und verwendung als arzneimittel |
| DE3606634A1 (de) | 1986-02-28 | 1987-09-03 | Mack Chem Pharm | Isohexid-nucleoside, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
| IT1204571B (it) * | 1987-05-08 | 1989-03-10 | Chiesi Farma Spa | Esteri di 1,4:3,6-dianidrosorbitolo-2-mononitrato e 5-mononitrato,loro procedimento di preparazione e loro composizioni farmaceutiche |
| DE3741005A1 (de) | 1987-12-03 | 1989-06-15 | Mack Chem Pharm | Aminopropanol-derivate von 1,4:3,6-dianhydro-hexit-nitraten, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
| US5428061A (en) | 1988-09-15 | 1995-06-27 | Schwarz Pharma Ag | Organic nitrates and method for their preparation |
| JP2628756B2 (ja) * | 1988-09-15 | 1997-07-09 | シュバルツファルマ アクチェンゲゼルシャフト | 新規有機ニトレート及びそれらの製造方法 |
| US4891373A (en) * | 1988-11-23 | 1990-01-02 | Pfizer Inc. | Aminopropanol derivatives of 1,4:3,6-dianhydrohexitol nitrates, processes for their preparation and their use as medicaments |
| CA2014520C (en) | 1989-04-17 | 1996-07-16 | Fumio Suzuki | Hexitol derivatives |
| NL9001955A (nl) * | 1990-09-05 | 1992-04-01 | Cedona Pharm Bv | Nieuwe thiazolidinederivaten. |
| FR2680173A1 (fr) * | 1991-08-07 | 1993-02-12 | Hoechst Lab | Nitrates organiques, leurs procedes de preparation et leur utilisation dans le traitement de maladies cardiovasculaires . |
| DK0656881T3 (da) * | 1992-07-30 | 1999-06-23 | Cal Int Ltd | Ester og kombinationer af et organisk nitrat og et salicylat |
| IL120531A (en) | 1997-03-26 | 2006-12-31 | Yissum Res Dev Co | Nitric oxide donors and pharmaceutical compositions containing them |
-
1998
- 1998-10-07 ES ES009802076A patent/ES2142773B1/es not_active Expired - Fee Related
-
1999
- 1999-09-30 AR ARP990104928A patent/AR020538A1/es active IP Right Grant
- 1999-10-04 NZ NZ510855A patent/NZ510855A/xx not_active IP Right Cessation
- 1999-10-04 GE GEAP19995886A patent/GEP20043162B/en unknown
- 1999-10-04 BR BRPI9914355-0A patent/BR9914355B1/pt not_active IP Right Cessation
- 1999-10-04 PE PE1999001005A patent/PE20001083A1/es not_active Application Discontinuation
- 1999-10-04 PL PL347030A patent/PL200028B1/pl not_active IP Right Cessation
- 1999-10-04 DE DE19983612T patent/DE19983612T1/de not_active Ceased
- 1999-10-04 EA EA200100422A patent/EA003360B1/ru not_active IP Right Cessation
- 1999-10-04 AU AU62041/99A patent/AU762724B2/en not_active Ceased
- 1999-10-04 JP JP2000574532A patent/JP4659214B2/ja not_active Expired - Fee Related
- 1999-10-04 WO PCT/ES1999/000316 patent/WO2000020420A1/es not_active Ceased
- 1999-10-04 HU HU0103937A patent/HUP0103937A3/hu unknown
- 1999-10-04 YU YU25201A patent/YU25201A/sh unknown
- 1999-10-04 ES ES99949015T patent/ES2257871T3/es not_active Expired - Lifetime
- 1999-10-04 CN CN99811802A patent/CN1096465C/zh not_active Expired - Fee Related
- 1999-10-04 DE DE69930949T patent/DE69930949T2/de not_active Expired - Lifetime
- 1999-10-04 DK DK99949015T patent/DK1120419T3/da active
- 1999-10-04 CA CA002346010A patent/CA2346010C/en not_active Expired - Fee Related
- 1999-10-04 GB GB0111172A patent/GB2359810B/en not_active Expired - Fee Related
- 1999-10-04 CZ CZ20011257A patent/CZ294551B6/cs not_active IP Right Cessation
- 1999-10-04 OA OA1200100085A patent/OA11661A/en unknown
- 1999-10-04 ID IDW00200101008A patent/ID29946A/id unknown
- 1999-10-04 PT PT99949015T patent/PT1120419E/pt unknown
- 1999-10-04 TR TR2001/00961T patent/TR200100961T2/xx unknown
- 1999-10-04 KR KR1020017004374A patent/KR100641801B1/ko not_active Expired - Fee Related
- 1999-10-04 AP APAP/P/2001/002128A patent/AP1555A/en active
- 1999-10-04 AT AT99949015T patent/ATE323707T1/de not_active IP Right Cessation
- 1999-10-04 RS YUP-252/01A patent/RS50112B/sr unknown
- 1999-10-04 EP EP99949015A patent/EP1120419B1/en not_active Expired - Lifetime
- 1999-10-04 HR HR20010256A patent/HRP20010256B1/xx not_active IP Right Cessation
- 1999-10-04 IL IL14239199A patent/IL142391A0/xx active IP Right Grant
- 1999-10-04 EE EEP200100207A patent/EE04374B1/xx not_active IP Right Cessation
- 1999-10-06 CO CO99063420A patent/CO5180544A1/es not_active Application Discontinuation
- 1999-10-07 PA PA19998483901A patent/PA8483901A1/es unknown
- 1999-10-07 GT GT199900173A patent/GT199900173A/es unknown
-
2001
- 2001-03-29 IS IS5910A patent/IS2312B/is unknown
- 2001-04-03 IL IL142391A patent/IL142391A/en not_active IP Right Cessation
- 2001-04-04 CU CU83A patent/CU23162A3/es not_active IP Right Cessation
- 2001-04-05 ZA ZA200102836A patent/ZA200102836B/xx unknown
- 2001-04-06 NO NO20011778A patent/NO328584B1/no not_active IP Right Cessation
- 2001-04-06 BG BG105417A patent/BG65135B1/bg unknown
- 2001-04-06 US US09/827,868 patent/US20010051735A1/en not_active Abandoned
-
2003
- 2003-04-28 US US10/424,828 patent/US6858632B2/en not_active Expired - Fee Related
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