JPH0414089B2 - - Google Patents
Info
- Publication number
- JPH0414089B2 JPH0414089B2 JP813483A JP813483A JPH0414089B2 JP H0414089 B2 JPH0414089 B2 JP H0414089B2 JP 813483 A JP813483 A JP 813483A JP 813483 A JP813483 A JP 813483A JP H0414089 B2 JPH0414089 B2 JP H0414089B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- lower alkyl
- crystals
- mmol
- 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
Links
- MDYOLVRUBBJPFM-UHFFFAOYSA-N Tropolone Natural products OC1=CC=CC=CC1=O MDYOLVRUBBJPFM-UHFFFAOYSA-N 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- -1 tropolone compound Chemical class 0.000 claims description 8
- 239000004480 active ingredient Substances 0.000 claims description 3
- 239000002246 antineoplastic agent Substances 0.000 claims description 3
- 229940041181 antineoplastic drug Drugs 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 239000013078 crystal Substances 0.000 description 19
- FUWUEFKEXZQKKA-UHFFFAOYSA-N beta-thujaplicin Chemical compound CC(C)C=1C=CC=C(O)C(=O)C=1 FUWUEFKEXZQKKA-UHFFFAOYSA-N 0.000 description 18
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 16
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 229930007845 β-thujaplicin Natural products 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 229910052786 argon Inorganic materials 0.000 description 8
- TUFYVOCKVJOUIR-UHFFFAOYSA-N alpha-Thujaplicin Natural products CC(C)C=1C=CC=CC(=O)C=1O TUFYVOCKVJOUIR-UHFFFAOYSA-N 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 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
- 238000010898 silica gel chromatography Methods 0.000 description 6
- 239000003814 drug Substances 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- 210000004027 cell Anatomy 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 3
- FBPNQPMYGLMRDR-UHFFFAOYSA-N 1-ethoxy-3,4-dihydro-1h-isochromene Chemical compound C1=CC=C2C(OCC)OCCC2=C1 FBPNQPMYGLMRDR-UHFFFAOYSA-N 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000012452 mother liquor Substances 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 230000004083 survival effect Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 230000000259 anti-tumor effect Effects 0.000 description 2
- 150000004699 copper complex Chemical class 0.000 description 2
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- OELWYQGRQUQQPD-IOMDMTNGSA-N (+)-(3R)-1-(3,4-dihydroxyphenyl)-7-phenyl-(6E)-6-hepten-3-ol Chemical compound C([C@@H](O)CCC=1C=C(O)C(O)=CC=1)C\C=C\C1=CC=CC=C1 OELWYQGRQUQQPD-IOMDMTNGSA-N 0.000 description 1
- WARCDZGSKKKAMZ-UHFFFAOYSA-N 1-(diethoxymethyl)-2-methylbenzene Chemical compound CCOC(OCC)C1=CC=CC=C1C WARCDZGSKKKAMZ-UHFFFAOYSA-N 0.000 description 1
- FTTLMNXOYOVHAG-UHFFFAOYSA-N 1-(diethoxymethyl)-4-methoxybenzene Chemical compound CCOC(OCC)C1=CC=C(OC)C=C1 FTTLMNXOYOVHAG-UHFFFAOYSA-N 0.000 description 1
- BVAOFFFFYDZUNU-UHFFFAOYSA-N 1-chloro-2-(diethoxymethyl)benzene Chemical compound CCOC(OCC)C1=CC=CC=C1Cl BVAOFFFFYDZUNU-UHFFFAOYSA-N 0.000 description 1
- 239000001431 2-methylbenzaldehyde Substances 0.000 description 1
- OURGENADILWNDO-UHFFFAOYSA-N 4-butyl-8-methyl-7-(2-oxocyclohexyl)oxychromen-2-one Chemical compound C1=CC=2C(CCCC)=CC(=O)OC=2C(C)=C1OC1CCCCC1=O OURGENADILWNDO-UHFFFAOYSA-N 0.000 description 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 102000004142 Trypsin Human genes 0.000 description 1
- 108090000631 Trypsin Proteins 0.000 description 1
- 230000009702 cancer cell proliferation Effects 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 230000004663 cell proliferation Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- MAQMEXSLUSZDQM-UHFFFAOYSA-N diethoxymethylbenzene Chemical compound CCOC(OCC)C1=CC=CC=C1 MAQMEXSLUSZDQM-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- FXLOVSHXALFLKQ-UHFFFAOYSA-N para-methylbenzaldehyde Natural products CC1=CC=C(C=O)C=C1 FXLOVSHXALFLKQ-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 150000004788 tropolones Chemical class 0.000 description 1
- 239000012588 trypsin Substances 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
Landscapes
- Pyrane Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- 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 |
|---|---|---|---|
| JP813483A JPS59134720A (ja) | 1983-01-20 | 1983-01-20 | 抗腫瘍薬 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP813483A JPS59134720A (ja) | 1983-01-20 | 1983-01-20 | 抗腫瘍薬 |
Related Child Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP18108783A Division JPS59134744A (ja) | 1983-09-28 | 1983-09-28 | 抗腫瘍作用を有するトロポロン誘導体 |
| JP58181088A Division JPS59134745A (ja) | 1983-09-28 | 1983-09-28 | 抗腫瘍作用を有するトロポロン誘導体 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59134720A JPS59134720A (ja) | 1984-08-02 |
| JPH0414089B2 true JPH0414089B2 (enrdf_load_stackoverflow) | 1992-03-11 |
Family
ID=11684813
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP813483A Granted JPS59134720A (ja) | 1983-01-20 | 1983-01-20 | 抗腫瘍薬 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59134720A (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9790158B2 (en) | 2012-06-22 | 2017-10-17 | University Of Connecticut | Substituted tropolone derivatives and methods of use |
-
1983
- 1983-01-20 JP JP813483A patent/JPS59134720A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS59134720A (ja) | 1984-08-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPS63275582A (ja) | ２−アミノイミダゾ〔４，５−ｂ〕ピリジン誘導体の製造方法 | |
| JPS59134745A (ja) | 抗腫瘍作用を有するトロポロン誘導体 | |
| RU2198875C2 (ru) | Способы получения тиосемикарбазонов пиридин-2-карбоксальдегидов и промежуточных пиридин-2-карбоксальдегидов | |
| JPH03109384A (ja) | （Ｓ）―４―ヒドロキシメチル―γ―ラクトンの製造方法 | |
| CA2491464A1 (en) | Process for preparation of 1,3-benzodioxole-2-spiro- cycloalkane derivatives | |
| JPS61129145A (ja) | ヒドロキノン誘導体及びその製造方法 | |
| JPH0414089B2 (enrdf_load_stackoverflow) | ||
| Kumari et al. | Studies on ylides exclusive formation of olefins from carbonyl compounds on treatment with para-bromo-and para-iodo-benzylidenetriphenylarsenanes | |
| Kelly et al. | 2, 2, 2-Triphenyl-4, 5-(2', 2"-biphenylene)-1, 3, 2-dioxaphospholane: an effective reagent for converting diols, amino alcohols, and especially mercapto alcohols to the corresponding heterocycles | |
| CN111253334A (zh) | 一种温和的c2醚取代2h-苯并噻唑衍生物的光催化合成方法 | |
| EP0062068B1 (en) | N-phthalidyl-5-fluorouracil derivatives | |
| SU1530094A3 (ru) | Способ получени конденсированных производных ас-триазина | |
| JP3432880B2 (ja) | 光学活性アザスピロ化合物の製法 | |
| JPH085880B2 (ja) | 抗生物質ジアザキノマイシンａ誘導体 | |
| JPS61215341A (ja) | 抗腫瘍活性トロポロン誘導体の製法 | |
| JPS59134744A (ja) | 抗腫瘍作用を有するトロポロン誘導体 | |
| JP2543703B2 (ja) | 有機ゲルマニウム化合物の製造方法 | |
| JPH0662470B2 (ja) | 光学活性ヘキサ−２，４−ジイン−１，６−ジオ−ル類の製法 | |
| JPH03275636A (ja) | シクロペンテン誘導体及びその製造中間体 | |
| SU470111A3 (ru) | Способ получени производных 5-(3"-фенил-1"-оксипропил)-6-диалкиламиноалкокси-4,7-диметоксибензофуранов | |
| JPH0692401B2 (ja) | １，４−ジヒドロピリジン誘導体 | |
| JPS6111231B2 (enrdf_load_stackoverflow) | ||
| JP2009280512A (ja) | ポリベンゾホスホール化合物とその製造方法 | |
| JPH04211646A (ja) | キノン誘導体 | |
| JPS62283970A (ja) | ２，３，５−三置換テトラヒドロフランの製造法 |