JPS6259706B2 - - Google Patents
Info
- Publication number
- JPS6259706B2 JPS6259706B2 JP16256478A JP16256478A JPS6259706B2 JP S6259706 B2 JPS6259706 B2 JP S6259706B2 JP 16256478 A JP16256478 A JP 16256478A JP 16256478 A JP16256478 A JP 16256478A JP S6259706 B2 JPS6259706 B2 JP S6259706B2
- Authority
- JP
- Japan
- Prior art keywords
- tpp
- cooh
- conjugate
- anticancer
- substance
- 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
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 7
- -1 thionyl halide Chemical class 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 5
- JZRYQZJSTWVBBD-UHFFFAOYSA-N pentaporphyrin i Chemical class N1C(C=C2NC(=CC3=NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 JZRYQZJSTWVBBD-UHFFFAOYSA-N 0.000 claims description 5
- 230000002140 halogenating effect Effects 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- AYEKOFBPNLCAJY-UHFFFAOYSA-O thiamine pyrophosphate Chemical compound CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N AYEKOFBPNLCAJY-UHFFFAOYSA-O 0.000 description 30
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 25
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- 239000000126 substance Substances 0.000 description 17
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 230000001093 anti-cancer Effects 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 10
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 235000019441 ethanol Nutrition 0.000 description 9
- VGQOVCHZGQWAOI-UHFFFAOYSA-N UNPD55612 Natural products N1C(O)C2CC(C=CC(N)=O)=CN2C(=O)C2=CC=C(C)C(O)=C12 VGQOVCHZGQWAOI-UHFFFAOYSA-N 0.000 description 8
- VGQOVCHZGQWAOI-HYUHUPJXSA-N anthramycin Chemical compound N1[C@@H](O)[C@@H]2CC(\C=C\C(N)=O)=CN2C(=O)C2=CC=C(C)C(O)=C12 VGQOVCHZGQWAOI-HYUHUPJXSA-N 0.000 description 8
- 229960004857 mitomycin Drugs 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- NWIBSHFKIJFRCO-WUDYKRTCSA-N Mytomycin Chemical compound C1N2C(C(C(C)=C(N)C3=O)=O)=C3[C@@H](COC(N)=O)[C@@]2(OC)[C@@H]2[C@H]1N2 NWIBSHFKIJFRCO-WUDYKRTCSA-N 0.000 description 6
- 206010028980 Neoplasm Diseases 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 238000000862 absorption spectrum Methods 0.000 description 5
- 239000002246 antineoplastic agent Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 229940041181 antineoplastic drug Drugs 0.000 description 4
- 201000011510 cancer Diseases 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- RKCAIXNGYQCCAL-UHFFFAOYSA-N porphin Chemical class N1C(C=C2N=C(C=C3NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 RKCAIXNGYQCCAL-UHFFFAOYSA-N 0.000 description 3
- 150000004032 porphyrins Chemical class 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- LPXQRXLUHJKZIE-UHFFFAOYSA-N 8-azaguanine Chemical compound NC1=NC(O)=C2NN=NC2=N1 LPXQRXLUHJKZIE-UHFFFAOYSA-N 0.000 description 2
- 229960005508 8-azaguanine Drugs 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 238000009825 accumulation Methods 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000001841 imino group Chemical group [H]N=* 0.000 description 2
- XELZGAJCZANUQH-UHFFFAOYSA-N methyl 1-acetylthieno[3,2-c]pyrazole-5-carboxylate Chemical compound CC(=O)N1N=CC2=C1C=C(C(=O)OC)S2 XELZGAJCZANUQH-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000013076 target substance Substances 0.000 description 2
- OGFAWKRXZLGJSK-UHFFFAOYSA-N 1-(2,4-dihydroxyphenyl)-2-(4-nitrophenyl)ethanone Chemical compound OC1=CC(O)=CC=C1C(=O)CC1=CC=C([N+]([O-])=O)C=C1 OGFAWKRXZLGJSK-UHFFFAOYSA-N 0.000 description 1
- KFKRXESVMDBTNQ-UHFFFAOYSA-N 3-[18-(2-carboxylatoethyl)-8,13-bis(1-hydroxyethyl)-3,7,12,17-tetramethyl-22,23-dihydroporphyrin-21,24-diium-2-yl]propanoate Chemical class N1C2=C(C)C(C(C)O)=C1C=C(N1)C(C)=C(C(O)C)C1=CC(C(C)=C1CCC(O)=O)=NC1=CC(C(CCC(O)=O)=C1C)=NC1=C2 KFKRXESVMDBTNQ-UHFFFAOYSA-N 0.000 description 1
- 206010003445 Ascites Diseases 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- UJKPHYRXOLRVJJ-MLSVHJFASA-N CC(O)C1=C(C)/C2=C/C3=N/C(=C\C4=C(CCC(O)=O)C(C)=C(N4)/C=C4\N=C(\C=C\1/N\2)C(C)=C4C(C)O)/C(CCC(O)=O)=C3C Chemical compound CC(O)C1=C(C)/C2=C/C3=N/C(=C\C4=C(CCC(O)=O)C(C)=C(N4)/C=C4\N=C(\C=C\1/N\2)C(C)=C4C(C)O)/C(CCC(O)=O)=C3C UJKPHYRXOLRVJJ-MLSVHJFASA-N 0.000 description 1
- 201000000274 Carcinosarcoma Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241001529936 Murinae Species 0.000 description 1
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 1
- 206010039491 Sarcoma Diseases 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Chemical group 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 230000003631 expected effect Effects 0.000 description 1
- 229960003569 hematoporphyrin Drugs 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- UXCDUFKZSUBXGM-UHFFFAOYSA-N phosphoric tribromide Chemical compound BrP(Br)(Br)=O UXCDUFKZSUBXGM-UHFFFAOYSA-N 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 150000004033 porphyrin derivatives Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Nitrogen Condensed Heterocyclic Rings (AREA)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP16256478A JPS5587792A (en) | 1978-12-27 | 1978-12-27 | Meso-tetra(p-carboxyphenyl)porphine derivative |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP16256478A JPS5587792A (en) | 1978-12-27 | 1978-12-27 | Meso-tetra(p-carboxyphenyl)porphine derivative |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS5587792A JPS5587792A (en) | 1980-07-02 |
JPS6259706B2 true JPS6259706B2 (de) | 1987-12-12 |
Family
ID=15756978
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP16256478A Granted JPS5587792A (en) | 1978-12-27 | 1978-12-27 | Meso-tetra(p-carboxyphenyl)porphine derivative |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS5587792A (de) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB8429845D0 (en) * | 1984-11-26 | 1985-01-03 | Efamol Ltd | Porphyrins & cancer treatment |
DE3688721T2 (de) * | 1985-04-30 | 1993-12-16 | Nippon Petrochemicals Co Ltd | Verwendung von Porphyrinderivaten bei der Entdeckung und Behandlung von Tumoren. |
EP3471774A4 (de) * | 2016-06-16 | 2020-04-15 | Oncoselect Therapeutics, LLC | Porphyrinverbindungen und zusammensetzungen zur behandlung von krebs |
-
1978
- 1978-12-27 JP JP16256478A patent/JPS5587792A/ja active Granted
Also Published As
Publication number | Publication date |
---|---|
JPS5587792A (en) | 1980-07-02 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN110092740B (zh) | 一种稠环化合物及其应用 | |
CN113683590B (zh) | 具有阿扎菲酮结构的偶联试剂及其在制备多肽、蛋白质偶联物中的应用 | |
US4863910A (en) | Complexes of AZO compounds and/or their salts and an antitumor agent and a method for reducing the growth of tumors | |
JPH03163055A (ja) | 特に医学画像形成に用いられる化合物および錯体 | |
JPS6259706B2 (de) | ||
CN109081852A (zh) | 一种双重靶向酞菁类抗癌光敏剂及其制备方法 | |
JPS6318592B2 (de) | ||
KR20210124328A (ko) | Pd-l1 면역조절제인 플루오로 비닐 벤즈아미드 화합물 | |
CN110627772A (zh) | 一种蒎烯稠合的手性三联吡啶双齿化合物及其制备方法 | |
JPS6326087B2 (de) | ||
JP4718444B2 (ja) | シクロブタン−1,1−ジカルボキシレートリガンドを有する白金錯体の蛋白結合誘導体 | |
WO2021219135A1 (zh) | 一种肌醇衍生物及其用途 | |
JPH06271577A (ja) | 2位置側鎖を有するテトラフェニルポルフィリン金属錯体及びその製造法 | |
US10723694B2 (en) | Propargyl-functionalized macrocyclic compounds | |
JP4249928B2 (ja) | 抗腫瘍剤としてのビス−(n,n’−ビス−(2−ハロエチル)アミノ)ホスホルアミデート | |
AU9195298A (en) | Binuclear complex | |
JPS6319515B2 (de) | ||
JP4511125B2 (ja) | フェニルアゾメチンデンドリマーとデンドロン誘導体の合成方法 | |
PL243397B1 (pl) | Reaktywne pochodne barwników Safirinium oraz ich zastosowanie | |
CN110551069B (zh) | 一种5-苯基戊醇类化合物及其中间体的合成方法 | |
EP0378706A1 (de) | 5-substituierte uridinderivate und zwischenprodukte | |
Zheng et al. | One-pot preparation of Fischer carbene complexes by solid-liquid phase transfer catalysis | |
JP4223601B2 (ja) | 新規ジピリルメテン化合物及びその製造方法 | |
JPH0375552B2 (de) | ||
JPS63277680A (ja) | ポルフィリン系化合物、その製造方法および該化合物を含む蛍光発色剤 |