JPH0680623A - Azo compound complex - Google Patents
Azo compound complexInfo
- Publication number
- JPH0680623A JPH0680623A JP3100893A JP10089391A JPH0680623A JP H0680623 A JPH0680623 A JP H0680623A JP 3100893 A JP3100893 A JP 3100893A JP 10089391 A JP10089391 A JP 10089391A JP H0680623 A JPH0680623 A JP H0680623A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- c2h4cl
- complex
- chemical
- 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
Links
- -1 Azo compound Chemical class 0.000 title claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 35
- JLIDBLDQVAYHNE-YKALOCIXSA-N (+)-Abscisic acid Chemical compound OC(=O)/C=C(/C)\C=C\[C@@]1(O)C(C)=CC(=O)CC1(C)C JLIDBLDQVAYHNE-YKALOCIXSA-N 0.000 claims abstract description 10
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims abstract description 6
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 claims abstract description 6
- 239000002246 antineoplastic agent Substances 0.000 claims abstract description 5
- FCRACOPGPMPSHN-UHFFFAOYSA-N desoxyabscisic acid Natural products OC(=O)C=C(C)C=CC1C(C)=CC(=O)CC1(C)C FCRACOPGPMPSHN-UHFFFAOYSA-N 0.000 claims abstract description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000003242 anti bacterial agent Substances 0.000 claims abstract description 4
- 230000003115 biocidal effect Effects 0.000 claims abstract description 4
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims abstract description 4
- 239000011976 maleic acid Substances 0.000 claims abstract description 4
- 150000003839 salts Chemical class 0.000 claims abstract description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims abstract description 4
- LCTORNIWLGOBPB-DVKNGEFBSA-N (2s,3r,4s,5s,6r)-2-amino-6-(hydroxymethyl)oxane-2,3,4,5-tetrol Chemical compound N[C@@]1(O)O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O LCTORNIWLGOBPB-DVKNGEFBSA-N 0.000 claims abstract description 3
- 229930182555 Penicillin Natural products 0.000 claims abstract description 3
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 claims abstract description 3
- CXKWCBBOMKCUKX-UHFFFAOYSA-M methylene blue Chemical compound [Cl-].C1=CC(N(C)C)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 CXKWCBBOMKCUKX-UHFFFAOYSA-M 0.000 claims abstract description 3
- 229960000907 methylthioninium chloride Drugs 0.000 claims abstract description 3
- 229940049954 penicillin Drugs 0.000 claims abstract description 3
- 229960005322 streptomycin Drugs 0.000 claims abstract description 3
- 239000000126 substance Substances 0.000 claims description 21
- GLVAUDGFNGKCSF-UHFFFAOYSA-N mercaptopurine Chemical compound S=C1NC=NC2=C1NC=N2 GLVAUDGFNGKCSF-UHFFFAOYSA-N 0.000 claims description 4
- ZXJXZNDDNMQXFV-UHFFFAOYSA-M crystal violet Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1[C+](C=1C=CC(=CC=1)N(C)C)C1=CC=C(N(C)C)C=C1 ZXJXZNDDNMQXFV-UHFFFAOYSA-M 0.000 claims description 3
- OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 claims description 3
- 229960005205 prednisolone Drugs 0.000 claims description 3
- KKAJSJJFBSOMGS-UHFFFAOYSA-N 3,6-diamino-10-methylacridinium chloride Chemical compound [Cl-].C1=C(N)C=C2[N+](C)=C(C=C(N)C=C3)C3=CC2=C1 KKAJSJJFBSOMGS-UHFFFAOYSA-N 0.000 claims description 2
- CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 claims description 2
- FOCVUCIESVLUNU-UHFFFAOYSA-N Thiotepa Chemical compound C1CN1P(N1CC1)(=S)N1CC1 FOCVUCIESVLUNU-UHFFFAOYSA-N 0.000 claims description 2
- JXLYSJRDGCGARV-WWYNWVTFSA-N Vinblastine Natural products O=C(O[C@H]1[C@](O)(C(=O)OC)[C@@H]2N(C)c3c(cc(c(OC)c3)[C@]3(C(=O)OC)c4[nH]c5c(c4CCN4C[C@](O)(CC)C[C@H](C3)C4)cccc5)[C@@]32[C@H]2[C@@]1(CC)C=CCN2CC3)C JXLYSJRDGCGARV-WWYNWVTFSA-N 0.000 claims description 2
- 229940023020 acriflavine Drugs 0.000 claims description 2
- 229960005091 chloramphenicol Drugs 0.000 claims description 2
- WIIZWVCIJKGZOK-RKDXNWHRSA-N chloramphenicol Chemical compound ClC(Cl)C(=O)N[C@H](CO)[C@H](O)C1=CC=C([N+]([O-])=O)C=C1 WIIZWVCIJKGZOK-RKDXNWHRSA-N 0.000 claims description 2
- 229960004397 cyclophosphamide Drugs 0.000 claims description 2
- 229960001428 mercaptopurine Drugs 0.000 claims description 2
- 239000000049 pigment Substances 0.000 claims description 2
- 229960001196 thiotepa Drugs 0.000 claims description 2
- 229960003048 vinblastine Drugs 0.000 claims description 2
- JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 claims description 2
- SNKDCTFPQUHAPR-UHFFFAOYSA-N 1-fluoropyrimidine-2,4-dione Chemical compound FN1C=CC(=O)NC1=O SNKDCTFPQUHAPR-UHFFFAOYSA-N 0.000 claims 1
- 239000000243 solution Substances 0.000 abstract description 13
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 abstract description 6
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 abstract description 4
- 239000003814 drug Substances 0.000 abstract description 3
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 abstract description 2
- GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 abstract description 2
- 230000004931 aggregating effect Effects 0.000 abstract description 2
- 229960002949 fluorouracil Drugs 0.000 abstract description 2
- 230000007721 medicinal effect Effects 0.000 abstract description 2
- 239000002904 solvent Substances 0.000 abstract description 2
- SNIOPGDIGTZGOP-UHFFFAOYSA-N Nitroglycerin Chemical compound [O-][N+](=O)OCC(O[N+]([O-])=O)CO[N+]([O-])=O SNIOPGDIGTZGOP-UHFFFAOYSA-N 0.000 abstract 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 229930182478 glucoside Natural products 0.000 abstract 1
- 150000008131 glucosides Chemical class 0.000 abstract 1
- 239000012266 salt solution Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000001632 sodium acetate Substances 0.000 description 4
- 235000017281 sodium acetate Nutrition 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- ZBIBQNVRTVLOHQ-UHFFFAOYSA-N 5-aminonaphthalen-1-ol Chemical compound C1=CC=C2C(N)=CC=CC2=C1O ZBIBQNVRTVLOHQ-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- 229910000365 copper sulfate Inorganic materials 0.000 description 2
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 1
- MSWZFWKMSRAUBD-QZABAPFNSA-N beta-D-glucosamine Chemical compound N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-QZABAPFNSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 238000003763 carbonization Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- NRONKADYZCLPCM-UHFFFAOYSA-N cyanic acid;potassium Chemical compound [K].OC#N NRONKADYZCLPCM-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 235000021395 porridge Nutrition 0.000 description 1
- GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- PVFOMCVHYWHZJE-UHFFFAOYSA-N trichloroacetyl chloride Chemical compound ClC(=O)C(Cl)(Cl)Cl PVFOMCVHYWHZJE-UHFFFAOYSA-N 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 0.000 description 1
- 229960001763 zinc sulfate Drugs 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は新規なアゾ化合物の複合
体に関し、この複合体は医薬等として有用である。FIELD OF THE INVENTION The present invention relates to a complex of a novel azo compound, and this complex is useful as a medicine or the like.
【０００２】[0002]
【従来の技術】本発明の複合体のごとき、アゾ化合物の
複合体は従来知られていない。2. Description of the Related Art A complex of an azo compound such as the complex of the present invention has not heretofore been known.
【０００３】[0003]
【発明が解決しようとする課題】従って本発明は、医薬
として又はその他種々の用途において有用な、アゾ化合
物の複合体を提供するものである。Accordingly, the present invention provides a complex of an azo compound which is useful as a medicine or in various other uses.
【０００４】[0004]
【課題を解決するための手段】上記の課題は、次の一般
式（Ｉ）：The above-mentioned problems are solved by the following general formula (I):
【化３】 [Chemical 3]
【化４】 で表わされる化合物又はその塩と、抗癌剤、抗生物質、
医療効果のある色素、アブシジン酸、マレイン酸、ｐ−
ヒドロキシ安息香酸、Ｄ−グルコースアミンもしくはグ
ルコシード又はこれらの組合せ、とから成る複合体を提
供することにより解決される。[Chemical 4] A compound represented by or a salt thereof, an anticancer agent, an antibiotic,
Medically effective pigments, abscisic acid, maleic acid, p-
The solution is to provide a complex consisting of hydroxybenzoic acid, D-glucose amine or glucoseed or a combination thereof.
【０００５】[0005]
【具体的な記載】本発明において使用する化合物として
は、例えば、ニトロミン、サイクロホスファマイド、チ
オテパ、６−メルカプトプリン、５−フルオルウラシー
ル、ビンブラスチン、Ｌ−アルパラギナーゼ、プレドニ
ゾロン等抗癌剤が挙げられる。Specific Description Examples of the compound used in the present invention include anticancer agents such as nitromine, cyclophosphamide, thiotepa, 6-mercaptopurine, 5-fluorouracil, vinblastine, L-alparaginase and prednisolone. .
【０００６】さらには、クロラムフェニコール、ストレ
プトマイシン、ペニシリン等の抗生物質が使用される。Further, antibiotics such as chloramphenicol, streptomycin and penicillin are used.
【０００７】また、医療効果のある色素化合物、例え
ば、ピオクタニン（メチールヴィオレット）、メチレン
ブルー、又はアクリフラビン等を用いることもできる。Further, a dye compound having a medical effect, such as pioctanine (methyl violet), methylene blue, or acriflavine, can be used.
【０００８】さらには、アブシジン酸、マレイン酸、ｐ
−ヒドロキシ安息香酸、Ｄ−グルコースアミン又はグル
コシード等を用いることもできる。これらを２種類以上
組合わせて使用することもできる。Furthermore, abscisic acid, maleic acid, p
-Hydroxybenzoic acid, D-glucosamine, glucoseed, etc. can also be used. It is also possible to use two or more of these in combination.
【０００９】本発明の複合体は、上記の活性化合物及び
式（Ｉ）で示される化合物の両者を、凝集性のある溶
媒、例えば２−メトキシエタノールに溶解した後、金属
塩、例えば硫酸マグネシウム、硫酸ナトリウム、硫酸亜
鉛、硫酸銅等、の溶液を添加するとにより極めて容易に
得られる。The complex of the present invention is obtained by dissolving both the above-mentioned active compound and the compound represented by the formula (I) in an aggregating solvent such as 2-methoxyethanol, and then dissolving the metal salt such as magnesium sulfate. It can be obtained very easily by adding a solution of sodium sulfate, zinc sulfate, copper sulfate or the like.
【００１０】本発明において使用する式（Ｉ）の化合物
は例えば、次の合成ルートにより合成することができ
る。The compound of formula (I) used in the present invention can be synthesized, for example, by the following synthetic route.
【００１１】[0011]
【化５】 [Chemical 5]
【００１２】上記式において、Ｒ，Ｒ′，Ｒ1 ，Ｒ2 及
びＲ3 はそれぞれ前記の意味を有する。次に、本発明の
化合物の製造方法を実施例により具体的に説明する。In the above formula, R, R ', R 1 , R 2 and R 3 each have the above meaning. Next, the method for producing the compound of the present invention will be specifically described with reference to Examples.
【００１３】実施例１．1.６グラムの５−アミノ−１−
ナフトールを50ccのピリジンに溶解し、10℃以下で１分
子量のトリクロロアセチルクロライドを滴下し化合せし
む。次にこれを一夜放置し翌日氷上に注ぐときは黒い沈
渣として化合物が得られる。このものを僅かに過剰のメ
チルフォルムアルデヒドと閉管中で 130℃に１−３時間
加熱する。 Embodiment 1. 1.6 grams of 5-amino-1-
Naphthol is dissolved in 50 cc of pyridine, and trichloroacetyl chloride having a molecular weight of 1 is added dropwise at 10 ° C or lower to combine. Then, when this is left overnight and poured on ice the next day, the compound is obtained as a black precipitate. This is heated to 130 ° C for 1-3 hours in a closed tube with a slight excess of methylformaldehyde.
【００１４】ここに生成した化合物を適量のアルコール
に溶解し別に公知の方法でヂアゾ化した２分子量のエチ
ルウレタン水溶液に注加する。つづいて５グラムの酢酸
ソーダを水に溶かして、これに加えると嵩の多い沈渣が
出来る。これを数時間又は一夜放置しておいてから濾過
乾燥すると暗黒色の水及びアルコールに溶けない次式で
表わされる化合物の粉末が得られる。The compound produced here is dissolved in an appropriate amount of alcohol and separately poured into a diazotized aqueous solution of ethyl urethane having a molecular weight of 2 by a known method. Next, dissolve 5 g of sodium acetate in water and add to it to form a bulky precipitate. If this is left for several hours or overnight and then filtered and dried, a powder of a compound represented by the following formula, which is insoluble in dark water and alcohol, is obtained.
【００１５】[0015]
【化６】 [Chemical 6]
【００１６】中途に於いて閉管中メチルフォルムアルデ
ヒドの代りにエチレンイミンを加える。 130℃に加熱
し、同一の操作をするときは次式化合物が得られる。In the middle of the tube, ethyleneimine is added instead of methylformaldehyde in a closed tube. When heated to 130 ° C. and carried out the same operation, the following compound of formula is obtained.
【００１７】[0017]
【化７】 [Chemical 7]
【００１８】上記の工程により得られた Form VIIIａの
化合物及びその等量のピオクタニン（メチルヴィオレッ
ト）とを２−メトキシエタノールに溶解し、それに硫酸
マグネシウム液を徐々に滴下するときは溶液は粥状にな
り、ついに固化するに至る。この時点で複合は完結した
ものである。ここに生成した化合物は水及びアルコール
に甚だよく溶解し、 200℃に於いて炭化し、次式の構造
式を有する。When the compound of Form VIIIa obtained by the above-mentioned step and its equivalent amount of pioctanine (methyl violet) are dissolved in 2-methoxyethanol, and magnesium sulfate solution is gradually added dropwise to the solution, the solution is porridge-like. And finally solidified. At this point the composite is complete. The compound formed here is very well dissolved in water and alcohol, carbonized at 200 ° C., and has the following structural formula.
【００１９】[0019]
【化８】 [Chemical 8]
【００２０】実施例２．1.６グラムの５−アミノ−１−
ナフトールをベンゼン５mlを２−クロルエチルエソシア
ナート５mlに加え化合せしむるときは直に化合し次式の
化合物が得られる。 Example 2. 1.6 grams of 5-amino-1-
When naphthol was mixed with 5 ml of benzene and 5 ml of 2-chloroethyl ethocyanate, the compound was directly combined to obtain the compound of the following formula.
【００２１】[0021]
【化９】 [Chemical 9]
【００２２】ここに生成した化合物を分離し、６グラム
のシアン酸加里とよく混合し、それに塩酸を攪拌しなが
ら滴下する。そして泡立ちがなくなるまで滴下し、一夜
放置しておく。それから反応物を水で処理して生成物を
濾過乾燥する。その化合物の構造式は次のとおりであ
る。The compound produced here is separated, mixed well with 6 g of potassium cyanate, and hydrochloric acid is added dropwise thereto with stirring. Then add dropwise until there is no bubbling and leave overnight. The reaction is then treated with water and the product filtered and dried. The structural formula of the compound is:
【００２３】[0023]
【化10】 [Chemical 10]
【００２４】ここに生成した化合物を 150mlのアルコー
ルに溶解する。これを公知の方法でヂアゾ化した２分子
量のスルファチトシン液中に注ぐ。これにつづいて５グ
ラムの酢酸ソーダを水に溶かして、これに加えると嵩の
多い沈渣が出来る。これを数時間又は一夜放置したのち
濾過乾燥する。その生成物は次の構造式を有する。The compound produced here is dissolved in 150 ml of alcohol. This is poured into a diazotized sulfacytosine solution having a molecular weight of 2 by a known method. Following this, 5 grams of sodium acetate is dissolved in water and added to this to form a bulky precipitate. This is left for several hours or overnight and then filtered and dried. The product has the following structural formula:
【００２５】[0025]
【化11】 [Chemical 11]
【００２６】次にこの生成物の適量の２−メトキシエタ
ノールに溶かしそれに１分子量のピオクタニンを加えて
溶解せしむ。そしてこれに徐々に苛性ソーダ液を滴下す
るときは、ワイン色にかわる。その時点で複合反応は終
る。ここに生成した化合物を分離乾燥する。このものは
水、アルコールに溶解し、 200℃において炭化分解す
る。その構造式は次式のごとくである。Next, this product is dissolved in an appropriate amount of 2-methoxyethanol, and 1 molecular weight of pioctanine is added thereto and dissolved. When gradually adding caustic soda solution to this, the wine color changes. At that point, the complex reaction ends. The compound produced here is separated and dried. This substance dissolves in water and alcohol and decomposes at 200 ℃. Its structural formula is as follows.
【００２７】[0027]
【化12】 [Chemical 12]
【００２８】実施例３．３グラムの５−アミノ−１−ナ
フトール20mlのヂオキサン、６mlの水、及び６グラムの
エチレンオキシードを閉管中に於いて２時間、30℃から
40℃に加熱する。ここに生成した化合物は次式の構造式
を有する。 Example 3. 3 grams of 5-amino-1-naphthol, 20 ml of dioxane, 6 ml of water, and 6 grams of ethylene oxide were stored in a closed tube for 2 hours at 30 ° C.
Heat to 40 ° C. The compound produced here has the following structural formula.
【００２９】[0029]
【化13】 [Chemical 13]
【００３０】ここに生成した化合物を公知の方法てヂア
ゾ化したスルファメチルアミン液に注ぐ、そしてつづい
て10グラムの酢酸ソーダを水に溶かし、これに加えると
きは、嵩の多い沈渣が出来る。それを濾過乾燥する。そ
の構造式は次のとおりである。When the compound formed here is poured into a solution of sulfamethylamine which has been diazotized by a known method, and then 10 g of sodium acetate is dissolved in water and added to this, a bulky precipitate is formed. It is filtered and dried. Its structural formula is:
【００３１】[0031]
【化14】 [Chemical 14]
【００３２】ここに生成した化合物をピリジン２mlを加
えたベンゼン50mlに溶解し、10mlのチオニールクロライ
ドをこれに滴下し化合せしむ。２時間の加熱で置換反応
は終る。ここに生成した化合物は次式の構造式を有す
る。The compound produced here is dissolved in 50 ml of benzene to which 2 ml of pyridine has been added, and 10 ml of thionyl chloride is added dropwise thereto to combine. The substitution reaction is completed by heating for 2 hours. The compound produced here has the following structural formula.
【００３３】[0033]
【化15】 [Chemical 15]
【００３４】更にここに生成した化合物を適量の２−メ
トキシエタノールに溶解し等量のプレードニゾロンを加
える。それから硫酸銅溶液を徐々に滴下するときは溶液
は粥状になる。この結晶生成が終ったとき複合反応は終
了する。ここに得られた生成物は水、アルコールに溶け
やすく、 200℃に於いて炭化分解する。その構造式は次
のごとくである。Further, the compound produced here is dissolved in an appropriate amount of 2-methoxyethanol, and an equal amount of prednisolone is added. Then, when the copper sulfate solution is gradually added dropwise, the solution becomes porridge-like. When this crystal formation is over, the complex reaction is over. The product obtained here is easily soluble in water and alcohol and decomposes by carbonization at 200 ° C. Its structural formula is as follows.
【００３５】[0035]
【化16】 [Chemical 16]
【００３６】実施例４．1.６グラムの５−アミノ−１−
ナフトールに５mlのベンゼンと５mlの２−クロロエチル
エソシアナートを加え化合せしむるときは直ちに化合
し、次のごとき化合物が得られる。 Example 4. 1.6 grams of 5-amino-1-
When 5 ml of benzene and 5 ml of 2-chloroethyl ethocyanate were added to naphthol and combined, the compounds were immediately combined to obtain the following compound.
【００３７】[0037]
【化17】 [Chemical 17]
【００３８】この化合物を分離し、６グラムのシアン酸
加里を加え、よく混合する。それを攪拌しながら塩酸を
滴下し、そして泡立ちがなくなるまで徐々に塩酸を滴下
する。このものを一夜放置する。この反応物を水で処理
し、沈澱物を濾過乾燥する。ここに生成せられた化合物
は次式のごとき構造式を有する。The compound is separated, 6 grams of cyanic acid potassium is added and mixed well. Hydrochloric acid is added dropwise with stirring, and hydrochloric acid is added slowly until no bubbles occur. Leave this one overnight. The reaction is treated with water and the precipitate is filtered and dried. The compound produced here has the following structural formula.
【００３９】[0039]
【化18】 [Chemical 18]
【００４０】ここに生成した化合物を 150mlのアルコー
ルに溶解し、これを２分子量の公知の方法によりヂアゾ
化したスルファイソシジン液に加え化合せしめ、つづい
て５グラムの酢酸ソーダを水に溶かし、これに加えると
直ちに嵩の多い沈渣が出来る。これを濾過乾燥する。そ
の化合物の構造式は次式のごとくである。The compound produced here was dissolved in 150 ml of alcohol, and this was added to a sulfazosidine solution diazotized by a known method of 2 molecular weight and combined, and then 5 g of sodium acetate was dissolved in water. When added to this, a bulky sediment is immediately formed. It is filtered and dried. The structural formula of the compound is as follows.
【００４１】[0041]
【化19】 [Chemical 19]
【００４２】以上によって得られた物質を２−メトシキ
エタノールに溶かし、これにピオクタニン、ピレドニゾ
ロン、アブシジン酸の等量を加え、これに硫酸マグネシ
ウム液を徐々に滴下するときは粥状になり、ついに凝固
するに至った。この時点で複合反応は終了する。ここに
於いて生成した化合物を分離乾燥にする。このものは水
溶性で 200℃で分解炭化する。その構造式は次式のごと
くである。The substance obtained as described above is dissolved in 2-methoxyethanol, and equal amounts of pioctanine, pyrednizolone and abscisic acid are added to this, and when a magnesium sulfate solution is slowly added dropwise, it becomes a porridge, and finally. It came to solidify. At this point the complex reaction is complete. The compound produced here is separated and dried. It is water-soluble and decomposes and carbonizes at 200 ° C. Its structural formula is as follows.
【００４３】[0043]
【化20】 [Chemical 20]
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.5 識別記号 庁内整理番号 ＦＩ 技術表示箇所 // Ａ６１Ｋ 31/655 ＡＤＵ 9360−4Ｃ ＡＤＺ 9360−4Ｃ ─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. 5 Identification code Office reference number FI technical display location // A61K 31/655 ADU 9360-4C ADZ 9360-4C
Claims (4)
医療効果のある色素、アブシジン酸、マレイン酸、ｐ−
ヒドロキシ安息香酸、Ｄ−グルコースアミンもしくはグ
ルコシード又はこれらの組合せ、とから成る複合体。1. The following general formula (I): [Chemical 2] A compound represented by or a salt thereof, an anticancer agent, an antibiotic,
Medically effective pigments, abscisic acid, maleic acid, p-
A complex consisting of hydroxybenzoic acid, D-glucose amine or glucoseed or a combination thereof.
スファマイド、チオテパ、６−メルカプトプリン、５−
フルオルウラシール、ビンブラスチン、Ｌ−アルパラギ
ナーゼ、又はプレドニゾロンである、請求項１に記載の
複合体。2. The anticancer agent is nitromine, cyclophosphamide, thiotepa, 6-mercaptopurine, 5-
The complex according to claim 1, which is fluoruracil, vinblastine, L-alparaginase, or prednisolone.
ル、ストレプトマイシン、又はペニシリンである、請求
項１に記載の複合体。3. The complex according to claim 1, wherein the antibiotic is chloramphenicol, streptomycin, or penicillin.
ン（メチールヴィオレット）、メチレンブルー、又はア
クリフラビンである、請求項１に記載の複合体。4. The complex according to claim 1, wherein the medically effective dye is pioctanine (methyl violet), methylene blue, or acriflavine.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61085900A JPS62242658A (en) | 1986-04-16 | 1986-04-16 | Production of azo complex |
| JP3100893A JPH0776206B2 (en) | 1986-04-16 | 1991-05-02 | Azo compound complex |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61085900A JPS62242658A (en) | 1986-04-16 | 1986-04-16 | Production of azo complex |
| JP3100893A JPH0776206B2 (en) | 1986-04-16 | 1991-05-02 | Azo compound complex |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61085900A Division JPS62242658A (en) | 1986-04-16 | 1986-04-16 | Production of azo complex |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0680623A true JPH0680623A (en) | 1994-03-22 |
| JPH0776206B2 JPH0776206B2 (en) | 1995-08-16 |
Family
ID=26426907
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61085900A Granted JPS62242658A (en) | 1986-04-16 | 1986-04-16 | Production of azo complex |
| JP3100893A Expired - Lifetime JPH0776206B2 (en) | 1986-04-16 | 1991-05-02 | Azo compound complex |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61085900A Granted JPS62242658A (en) | 1986-04-16 | 1986-04-16 | Production of azo complex |
Country Status (1)
| Country | Link |
|---|---|
| JP (2) | JPS62242658A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005517460A (en) * | 2000-05-10 | 2005-06-16 | アッシュ・アクセス・テクノロジー・インコーポレーテッド | Catheter lock solution containing photooxidizer |
| WO2009084982A1 (en) * | 2007-12-28 | 2009-07-09 | Mikhail Vladimirovich Kutushov | Use of organic dyes as an agent for treating oncological diseases |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104327546A (en) * | 2014-10-16 | 2015-02-04 | 天津德凯化工股份有限公司 | Dye reactive brown and preparation method thereof |
-
1986
- 1986-04-16 JP JP61085900A patent/JPS62242658A/en active Granted
-
1991
- 1991-05-02 JP JP3100893A patent/JPH0776206B2/en not_active Expired - Lifetime
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005517460A (en) * | 2000-05-10 | 2005-06-16 | アッシュ・アクセス・テクノロジー・インコーポレーテッド | Catheter lock solution containing photooxidizer |
| WO2009084982A1 (en) * | 2007-12-28 | 2009-07-09 | Mikhail Vladimirovich Kutushov | Use of organic dyes as an agent for treating oncological diseases |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS62242658A (en) | 1987-10-23 |
| JPH0529219B2 (en) | 1993-04-28 |
| JPH0776206B2 (en) | 1995-08-16 |
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| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |