JPH0510336B2 - - Google Patents
Info
- Publication number
- JPH0510336B2 JPH0510336B2 JP59055784A JP5578484A JPH0510336B2 JP H0510336 B2 JPH0510336 B2 JP H0510336B2 JP 59055784 A JP59055784 A JP 59055784A JP 5578484 A JP5578484 A JP 5578484A JP H0510336 B2 JPH0510336 B2 JP H0510336B2
- Authority
- JP
- Japan
- Prior art keywords
- reduced pressure
- under reduced
- ethyl acetate
- aromatic
- boc
- 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.)
- Expired - Lifetime
Links
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 125000003118 aryl group Chemical group 0.000 description 15
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 239000007787 solid Substances 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 238000001816 cooling Methods 0.000 description 7
- 238000000921 elemental analysis Methods 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- 238000010898 silica gel chromatography Methods 0.000 description 5
- NRKYWOKHZRQRJR-UHFFFAOYSA-N 2,2,2-trifluoroacetamide Chemical compound NC(=O)C(F)(F)F NRKYWOKHZRQRJR-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 4
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 230000000259 anti-tumor effect Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- FUKUFMFMCZIRNT-UHFFFAOYSA-N hydron;methanol;chloride Chemical compound Cl.OC FUKUFMFMCZIRNT-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- -1 trifluoroacetyl compound Chemical class 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- FXXOWMASCSSPPJ-UHFFFAOYSA-N 1-amino-2-ethylanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=C(N)C(CC)=CC=C3C(=O)C2=C1 FXXOWMASCSSPPJ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- YUENFNPLGJCNRB-UHFFFAOYSA-N anthracen-1-amine Chemical class C1=CC=C2C=C3C(N)=CC=CC3=CC2=C1 YUENFNPLGJCNRB-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- UICWSWIMNYSQKK-UHFFFAOYSA-N benzhydrylbenzene;hydrochloride Chemical compound Cl.C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 UICWSWIMNYSQKK-UHFFFAOYSA-N 0.000 description 1
- ZYBWTEQKHIADDQ-UHFFFAOYSA-N ethanol;methanol Chemical compound OC.CCO ZYBWTEQKHIADDQ-UHFFFAOYSA-N 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 1
- DMRGXAJTPVLUEX-UHFFFAOYSA-N tert-butyl N-[2-[[5,8-dihydroxy-4-[2-[2-hydroxyethyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]ethylamino]-9,10-dioxoanthracen-1-yl]amino]ethyl]-N-(2-hydroxyethyl)carbamate Chemical compound CC(C)(C)OC(=O)N(CCO)CCNC1=CC=C(NCCN(CCO)C(=O)OC(C)(C)C)C2=C1C(=O)C1=C(O)C=CC(O)=C1C2=O DMRGXAJTPVLUEX-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
Landscapes
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5578484A JPS60199863A (ja) | 1984-03-23 | 1984-03-23 | アミノアンスラセン誘導体 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5578484A JPS60199863A (ja) | 1984-03-23 | 1984-03-23 | アミノアンスラセン誘導体 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60199863A JPS60199863A (ja) | 1985-10-09 |
| JPH0510336B2 true JPH0510336B2 (ru) | 1993-02-09 |
Family
ID=13008525
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5578484A Granted JPS60199863A (ja) | 1984-03-23 | 1984-03-23 | アミノアンスラセン誘導体 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60199863A (ru) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9828670D0 (en) * | 1998-12-24 | 1999-02-17 | Univ Montfort | Anthraquinone anticancer drugs |
| KR100324644B1 (ko) * | 1999-10-26 | 2002-02-27 | 박호군 | α-아미노안트라센 유도체 및 그의 공중합체와, 이를 이용한 형광 화상 형성 방법 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4197249A (en) * | 1977-08-15 | 1980-04-08 | American Cyanamid Company | 1,4-Bis(substituted-amino)-5,8-dihydroxyanthraquinones and leuco bases thereof |
| JPS591453A (ja) * | 1982-06-28 | 1984-01-06 | Dai Ichi Seiyaku Co Ltd | アンスラセンジオン誘導体 |
-
1984
- 1984-03-23 JP JP5578484A patent/JPS60199863A/ja active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4197249A (en) * | 1977-08-15 | 1980-04-08 | American Cyanamid Company | 1,4-Bis(substituted-amino)-5,8-dihydroxyanthraquinones and leuco bases thereof |
| JPS591453A (ja) * | 1982-06-28 | 1984-01-06 | Dai Ichi Seiyaku Co Ltd | アンスラセンジオン誘導体 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60199863A (ja) | 1985-10-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA3059135A1 (en) | Synthesis of polycyclic-carbamoylpyridone compounds | |
| CZ25399A3 (cs) | Způsob výroby trijodbenzendikarboxamidových derivátů | |
| WO2021013795A2 (en) | Method of making nicotinamide ribofuranoside salts, nicotinamide ribofuranoside salts as such, and uses thereof | |
| JP2004530638A (ja) | 結晶性ベンラファクシン塩基、及び新規なベンラファクシン塩酸塩多型形状、ならびにその調製方法 | |
| JPH0510336B2 (ru) | ||
| PT91205B (pt) | Processo para a preparacao de 2-aminopurina | |
| US6545149B2 (en) | Synthesis and crystallization of piperazine ring-containing compounds | |
| KR20110091534A (ko) | 모르핀-6-글루쿠로니드 또는 그의 유도체 중 하나의 합성 | |
| CN112939814A (zh) | 一种氘代达卡他韦中间体的制备方法 | |
| JP2000503666A (ja) | Ｍａｐｐｉａ ｆｏｅｔｉｄａから単離したカンプトセシン―骨格化合物および新規な医薬ならびに治療薬のためのシントンとしてのその使用 | |
| US3058992A (en) | Intermediates for the preparation of | |
| US6861525B2 (en) | Process for the preparation imidazo[1,2-A]pyridine-3-acetamides | |
| KR0157422B1 (ko) | 6-(3-디메틸아미노프로피오닐)포르스콜린 제조방법 | |
| WO1998041532A1 (en) | Erythromycin a oxime dihydrate | |
| US6008413A (en) | Process for recrystallizing 1,3-bis(aminophenoxy benzene) | |
| JPS58135884A (ja) | ビンカミン酸エステルの製造方法 | |
| US3152123A (en) | Process for the preparation of benzo- | |
| US3751462A (en) | Process for preparation of substituted fluoromethanesulfonanilides | |
| JPH05279305A (ja) | ３′−アミノ−２′−ヒドロキシアセトフェノンの製造方法 | |
| WO1999055660A1 (en) | Process for the preparation of aceclofenac | |
| JPH0219819B2 (ru) | ||
| JP3107427B2 (ja) | グルタチオンモノエステル塩およびその製法 | |
| US2463831A (en) | Amino alkyl benzoates | |
| US20040176591A1 (en) | Novel synthesis and crystallization of peperazine ring-containing compounds | |
| HU191693B (en) | Process for production of derivatives of 9-or-11 substituated apovincamin acid |