CN104086554B - 一种新型的完全水溶的光敏剂单体及其制备方法及应用 - Google Patents
一种新型的完全水溶的光敏剂单体及其制备方法及应用 Download PDFInfo
- Publication number
- CN104086554B CN104086554B CN201410238812.XA CN201410238812A CN104086554B CN 104086554 B CN104086554 B CN 104086554B CN 201410238812 A CN201410238812 A CN 201410238812A CN 104086554 B CN104086554 B CN 104086554B
- Authority
- CN
- China
- Prior art keywords
- water
- formula
- acetonitrile
- enfoliative
- cytologic
- 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.)
- Active
Links
- 239000000178 monomer Substances 0.000 title claims abstract description 18
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- 239000003504 photosensitizing agent Substances 0.000 title abstract description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 47
- 150000003839 salts Chemical class 0.000 claims abstract description 25
- 238000000034 method Methods 0.000 claims abstract description 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 18
- 229910052700 potassium Inorganic materials 0.000 claims abstract description 15
- ATNHDLDRLWWWCB-AENOIHSZSA-M chlorophyll a Chemical compound C1([C@@H](C(=O)OC)C(=O)C2=C3C)=C2N2C3=CC(C(CC)=C3C)=[N+]4C3=CC3=C(C=C)C(C)=C5N3[Mg-2]42[N+]2=C1[C@@H](CCC(=O)OC\C=C(/C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)[C@H](C)C2=C5 ATNHDLDRLWWWCB-AENOIHSZSA-M 0.000 claims abstract description 12
- 229930002868 chlorophyll a Natural products 0.000 claims abstract description 10
- 229910052708 sodium Inorganic materials 0.000 claims abstract description 8
- 239000002994 raw material Substances 0.000 claims abstract description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 51
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 48
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 40
- 150000001875 compounds Chemical class 0.000 claims description 33
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 28
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 26
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 20
- 238000000605 extraction Methods 0.000 claims description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 17
- 239000002904 solvent Substances 0.000 claims description 16
- 238000002425 crystallisation Methods 0.000 claims description 13
- 230000008025 crystallization Effects 0.000 claims description 13
- 235000015112 vegetable and seed oil Nutrition 0.000 claims description 13
- 239000008158 vegetable oil Substances 0.000 claims description 13
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 12
- 239000003960 organic solvent Substances 0.000 claims description 12
- 238000003756 stirring Methods 0.000 claims description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 10
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 claims description 10
- 239000007788 liquid Substances 0.000 claims description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
- 239000007864 aqueous solution Substances 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 8
- 239000007787 solid Substances 0.000 claims description 8
- 239000000243 solution Substances 0.000 claims description 8
- 238000001514 detection method Methods 0.000 claims description 7
- 239000011259 mixed solution Substances 0.000 claims description 7
- 239000011734 sodium Substances 0.000 claims description 7
- 238000001914 filtration Methods 0.000 claims description 6
- 238000004587 chromatography analysis Methods 0.000 claims description 5
- 238000004090 dissolution Methods 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 5
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 4
- 239000000908 ammonium hydroxide Substances 0.000 claims description 4
- 238000000746 purification Methods 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- 238000010898 silica gel chromatography Methods 0.000 claims description 4
- 238000000638 solvent extraction Methods 0.000 claims description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 3
- 239000013078 crystal Substances 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 239000012046 mixed solvent Substances 0.000 claims description 3
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 3
- 235000015320 potassium carbonate Nutrition 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- 239000000741 silica gel Substances 0.000 claims description 3
- 229910002027 silica gel Inorganic materials 0.000 claims description 3
- 238000001291 vacuum drying Methods 0.000 claims description 3
- 239000000945 filler Substances 0.000 claims description 2
- 238000005498 polishing Methods 0.000 claims description 2
- 201000011510 cancer Diseases 0.000 abstract description 8
- 239000003814 drug Substances 0.000 abstract description 6
- 230000003902 lesion Effects 0.000 abstract description 6
- 238000002428 photodynamic therapy Methods 0.000 abstract description 6
- 206010034972 Photosensitivity reaction Diseases 0.000 abstract description 3
- 230000036211 photosensitivity Effects 0.000 abstract description 3
- NSFSLUUZQIAOOX-LDCXZXNSSA-N pheophorbide a Chemical compound N1C(C=C2[C@H]([C@H](CCC(O)=O)C(=N2)C2=C3NC(=C4)C(C)=C3C(=O)[C@@H]2C(=O)OC)C)=C(C)C(C=C)=C1C=C1C(C)=C(CC)C4=N1 NSFSLUUZQIAOOX-LDCXZXNSSA-N 0.000 abstract description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 abstract 1
- 239000012071 phase Substances 0.000 description 16
- 239000011591 potassium Substances 0.000 description 12
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 11
- 150000003863 ammonium salts Chemical class 0.000 description 10
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 7
- 206010028980 Neoplasm Diseases 0.000 description 7
- 238000004128 high performance liquid chromatography Methods 0.000 description 7
- PUUBADHCONCMPA-USOGPTGWSA-N 3-[(21S,22S)-11-ethyl-16-(1-hexoxyethyl)-4-hydroxy-12,17,21,26-tetramethyl-7,23,24,25-tetrazahexacyclo[18.2.1.15,8.110,13.115,18.02,6]hexacosa-1,4,6,8(26),9,11,13(25),14,16,18(24),19-undecaen-22-yl]propanoic acid Chemical compound CCCCCCOC(C)C1=C(C2=NC1=CC3=NC(=CC4=C(C5=C(CC(=C6[C@H]([C@@H](C(=C2)N6)C)CCC(=O)O)C5=N4)O)C)C(=C3C)CC)C PUUBADHCONCMPA-USOGPTGWSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 159000000000 sodium salts Chemical class 0.000 description 5
- SURLGNKAQXKNSP-DBLYXWCISA-N chlorin Chemical compound C\1=C/2\N/C(=C\C3=N/C(=C\C=4NC(/C=C\5/C=CC/1=N/5)=CC=4)/C=C3)/CC\2 SURLGNKAQXKNSP-DBLYXWCISA-N 0.000 description 4
- 238000010828 elution Methods 0.000 description 3
- 239000008194 pharmaceutical composition Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- SOBHUZYZLFQYFK-UHFFFAOYSA-K trisodium;hydroxy-[[phosphonatomethyl(phosphonomethyl)amino]methyl]phosphinate Chemical compound [Na+].[Na+].[Na+].OP(O)(=O)CN(CP(O)([O-])=O)CP([O-])([O-])=O SOBHUZYZLFQYFK-UHFFFAOYSA-K 0.000 description 3
- 235000016425 Arthrospira platensis Nutrition 0.000 description 2
- 240000002900 Arthrospira platensis Species 0.000 description 2
- 206010006187 Breast cancer Diseases 0.000 description 2
- 208000026310 Breast neoplasm Diseases 0.000 description 2
- 101000576973 Homo sapiens Mitochondrial-processing peptidase subunit beta Proteins 0.000 description 2
- 102100025298 Mitochondrial-processing peptidase subunit beta Human genes 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 2
- 238000006114 decarboxylation reaction Methods 0.000 description 2
- 229960000935 dehydrated alcohol Drugs 0.000 description 2
- 229960004756 ethanol Drugs 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 238000005374 membrane filtration Methods 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 229940082787 spirulina Drugs 0.000 description 2
- -1 trimethylammonium ester Chemical class 0.000 description 2
- BPIUIOXAFBGMNB-UHFFFAOYSA-N 1-hexoxyhexane Chemical group CCCCCCOCCCCCC BPIUIOXAFBGMNB-UHFFFAOYSA-N 0.000 description 1
- FDKRLXBXYZKWRZ-UWJYYQICSA-N 3-[(21S,22S)-16-ethenyl-11-ethyl-4-hydroxy-12,17,21,26-tetramethyl-7,23,24,25-tetrazahexacyclo[18.2.1.15,8.110,13.115,18.02,6]hexacosa-1,4,6,8(26),9,11,13(25),14,16,18(24),19-undecaen-22-yl]propanoic acid Chemical compound CCC1=C(C2=NC1=CC3=C(C4=C(CC(=C5[C@H]([C@@H](C(=CC6=NC(=C2)C(=C6C)C=C)N5)C)CCC(=O)O)C4=N3)O)C)C FDKRLXBXYZKWRZ-UWJYYQICSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 208000037260 Atherosclerotic Plaque Diseases 0.000 description 1
- 239000002028 Biomass Substances 0.000 description 1
- 206010005003 Bladder cancer Diseases 0.000 description 1
- JUDGRMABQJKRPW-XIADSQHASA-N CCC1=C(/C=C2\N=C(/C(\CC3=O)=C(/[C@@H](CCC(O)=O)[C@@H]4C)\N/C\4=C\C(C(C)=C4C=C)=N/C\4=C4)C3=C\2C)NC/4=C1C Chemical compound CCC1=C(/C=C2\N=C(/C(\CC3=O)=C(/[C@@H](CCC(O)=O)[C@@H]4C)\N/C\4=C\C(C(C)=C4C=C)=N/C\4=C4)C3=C\2C)NC/4=C1C JUDGRMABQJKRPW-XIADSQHASA-N 0.000 description 1
- 208000017897 Carcinoma of esophagus Diseases 0.000 description 1
- 206010008342 Cervix carcinoma Diseases 0.000 description 1
- 235000000751 Chenopodium murale Nutrition 0.000 description 1
- 244000191502 Chenopodium murale Species 0.000 description 1
- 208000032170 Congenital Abnormalities Diseases 0.000 description 1
- 206010061619 Deformity Diseases 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 208000007766 Kaposi sarcoma Diseases 0.000 description 1
- 208000032271 Malignant tumor of penis Diseases 0.000 description 1
- 206010027476 Metastases Diseases 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 208000002454 Nasopharyngeal Carcinoma Diseases 0.000 description 1
- 206010061306 Nasopharyngeal cancer Diseases 0.000 description 1
- 206010030155 Oesophageal carcinoma Diseases 0.000 description 1
- 208000004179 Oral Leukoplakia Diseases 0.000 description 1
- 208000002471 Penile Neoplasms Diseases 0.000 description 1
- 206010034299 Penile cancer Diseases 0.000 description 1
- 206010035603 Pleural mesothelioma Diseases 0.000 description 1
- 206010060862 Prostate cancer Diseases 0.000 description 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- 208000027073 Stargardt disease Diseases 0.000 description 1
- 208000005718 Stomach Neoplasms Diseases 0.000 description 1
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 description 1
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 208000003362 bronchogenic carcinoma Diseases 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 201000010881 cervical cancer Diseases 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229930002875 chlorophyll Natural products 0.000 description 1
- 235000019804 chlorophyll Nutrition 0.000 description 1
- 208000006990 cholangiocarcinoma Diseases 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 238000011097 chromatography purification Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000003745 diagnosis Methods 0.000 description 1
- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 1
- 229910000396 dipotassium phosphate Inorganic materials 0.000 description 1
- 235000019797 dipotassium phosphate Nutrition 0.000 description 1
- 238000002072 distortionless enhancement with polarization transfer spectrum Methods 0.000 description 1
- 230000002500 effect on skin Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 201000005619 esophageal carcinoma Diseases 0.000 description 1
- 208000021045 exocrine pancreatic carcinoma Diseases 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
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 201000007270 liver cancer Diseases 0.000 description 1
- 208000014018 liver neoplasm Diseases 0.000 description 1
- 206010025135 lupus erythematosus Diseases 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 201000001441 melanoma Diseases 0.000 description 1
- 230000009401 metastasis Effects 0.000 description 1
- OKKJLVBELUTLKV-VMNATFBRSA-N methanol-d1 Chemical compound [2H]OC OKKJLVBELUTLKV-VMNATFBRSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 210000004088 microvessel Anatomy 0.000 description 1
- 201000011216 nasopharynx carcinoma Diseases 0.000 description 1
- 208000018389 neoplasm of cerebral hemisphere Diseases 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 201000008557 oral mucosa leukoplakia Diseases 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- BBNQQADTFFCFGB-UHFFFAOYSA-N purpurin Chemical compound C1=CC=C2C(=O)C3=C(O)C(O)=CC(O)=C3C(=O)C2=C1 BBNQQADTFFCFGB-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 201000000849 skin cancer Diseases 0.000 description 1
- 201000008261 skin carcinoma Diseases 0.000 description 1
- 206010040882 skin lesion Diseases 0.000 description 1
- 231100000444 skin lesion Toxicity 0.000 description 1
- 238000000935 solvent evaporation Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 201000000498 stomach carcinoma Diseases 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 201000005112 urinary bladder cancer Diseases 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains four or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K41/00—Medicinal preparations obtained by treating materials with wave energy or particle radiation ; Therapies using these preparations
- A61K41/0057—Photodynamic therapy with a photosensitizer, i.e. agent able to produce reactive oxygen species upon exposure to light or radiation, e.g. UV or visible light; photocleavage of nucleic acids with an agent
- A61K41/0071—PDT with porphyrins having exactly 20 ring atoms, i.e. based on the non-expanded tetrapyrrolic ring system, e.g. bacteriochlorin, chlorin-e6, or phthalocyanines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Biochemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
时间(min) | 流动相A(%) | 流动相B(%) |
0 | 50 | 50 |
5 | 50 | 50 |
20 | 30 | 70 |
25 | 30 | 70 |
25.5 | 50 | 50 |
Claims (2)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201410238812.XA CN104086554B (zh) | 2014-05-30 | 2014-05-30 | 一种新型的完全水溶的光敏剂单体及其制备方法及应用 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201410238812.XA CN104086554B (zh) | 2014-05-30 | 2014-05-30 | 一种新型的完全水溶的光敏剂单体及其制备方法及应用 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN104086554A CN104086554A (zh) | 2014-10-08 |
CN104086554B true CN104086554B (zh) | 2016-02-17 |
Family
ID=51634342
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201410238812.XA Active CN104086554B (zh) | 2014-05-30 | 2014-05-30 | 一种新型的完全水溶的光敏剂单体及其制备方法及应用 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN104086554B (zh) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN106279051A (zh) * | 2016-08-11 | 2017-01-04 | 重庆大学 | 一类水性的含查耳酮‑苯并三氮唑二联体的可见光光敏剂 |
CN107987081B (zh) * | 2016-10-26 | 2019-12-06 | 刘辉 | 一种二氢卟吩e6衍生物及其药学上可接受的盐、其制备方法和应用 |
US9951081B1 (en) | 2016-10-26 | 2018-04-24 | Hui Liu | Chlorin e6 derivative and pharmaceutically acceptable salt thereof and process for preparing and use of the same |
CN108840907A (zh) * | 2018-05-22 | 2018-11-20 | 桂林市兴达光电医疗器械有限公司 | 酪丝亮肽-脱镁叶绿酸a单酯及其制备方法 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1990000895A1 (en) * | 1988-07-20 | 1990-02-08 | Health Research, Inc. | New photosensitizing agents |
CN1102412A (zh) * | 1994-06-03 | 1995-05-10 | 中国人民解放军第二军医大学 | 二氢卟吩e6醚衍生物及其合成方法 |
CN101638411A (zh) * | 2001-06-01 | 2010-02-03 | 塞拉莫普泰克工业公司 | 用于光动力学治疗的水溶性卟啉盐的制备方法 |
CN102268004A (zh) * | 2011-06-21 | 2011-12-07 | 北京普瑞博思投资有限公司 | 一种叶绿酸盐化合物及其制备方法 |
-
2014
- 2014-05-30 CN CN201410238812.XA patent/CN104086554B/zh active Active
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1990000895A1 (en) * | 1988-07-20 | 1990-02-08 | Health Research, Inc. | New photosensitizing agents |
CN1102412A (zh) * | 1994-06-03 | 1995-05-10 | 中国人民解放军第二军医大学 | 二氢卟吩e6醚衍生物及其合成方法 |
CN101638411A (zh) * | 2001-06-01 | 2010-02-03 | 塞拉莫普泰克工业公司 | 用于光动力学治疗的水溶性卟啉盐的制备方法 |
CN102268004A (zh) * | 2011-06-21 | 2011-12-07 | 北京普瑞博思投资有限公司 | 一种叶绿酸盐化合物及其制备方法 |
Also Published As
Publication number | Publication date |
---|---|
CN104086554A (zh) | 2014-10-08 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN104447739B (zh) | 一种氘代Palbociclib衍生物、制备方法及应用 | |
CN104086554B (zh) | 一种新型的完全水溶的光敏剂单体及其制备方法及应用 | |
CN105884726B (zh) | 丁苯酞的合成方法和纯化工艺 | |
CN103360240A (zh) | 一种高纯度非诺贝酸的制备方法 | |
CN106810555B (zh) | 一种利用金属还原剂由氧化苦参碱制备苦参碱的方法 | |
CN105693605A (zh) | 一种光学纯(r)/(s)-氯喹的不对称合成方法 | |
CN107163060A (zh) | 一种硫酸氢氯吡格雷晶型ii制备方法 | |
CN101195602B (zh) | 1-脱氧野尻毒素衍生物、其制备方法及其应用 | |
CN101817827A (zh) | 一种从芝麻中制备芝麻素的方法 | |
CN111039910A (zh) | 一种光引发的合成3-芳基黄酮或香豆素类化合物的方法及应用 | |
CN110105195A (zh) | 一种从青蒿蜡油中提取二氢青蒿酸的方法 | |
CN103848803A (zh) | 黄芩素烟酰胺共晶 | |
CN106588757B (zh) | 一种羟基吡啶酮类贫铀促排剂及其制备方法和用途 | |
CN111848709B (zh) | 一种新型异戊烯基黄酮类化合物及其制备方法和应用 | |
CN108840816A (zh) | 酰亚胺类中间体化合物及其制备方法和应用 | |
CN101270119B (zh) | 一种从豆科棘豆属或黄芪属植物中提纯苦马豆素的工艺 | |
CN103102281A (zh) | 一种琥珀酸美托洛尔的合成方法 | |
CN107540589A (zh) | 一种艾尔骨化醇晶型、药物组合物及制备方法和应用 | |
CN105949146A (zh) | 截短侧耳素-替唑尼特杂合药物及其制备方法 | |
CN103006670B (zh) | 一种总不饱和蟾蜍内酯及其制备方法和用途 | |
CN104098523B (zh) | 1-异丁酰基-3-苯基-1,4-二氢-1,2,4,5-四嗪及制备和应用 | |
CN110075145B (zh) | 一种从夹竹桃叶中提取总强心苷的方法 | |
CN113912492B (zh) | 一种氟比洛芬酯的精制方法 | |
WO2022067724A1 (zh) | 一种sglt-2抑制剂·肌氨酸共晶体及其制备方法和应用 | |
CN102786472A (zh) | 利用超临界萃取-结晶技术提取分离千层塔及其毛状根中石杉碱甲的方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: Novel photosensitizer monomer completely soluble in water, and preparation method and application thereof Effective date of registration: 20160826 Granted publication date: 20160217 Pledgee: Guilin SME credit Company Limited by Guarantee Pledgor: Guilin Huiang Biochemistry Pharmaceutical Co.,Ltd. Registration number: 2016450000012 |
|
PLDC | Enforcement, change and cancellation of contracts on pledge of patent right or utility model | ||
PC01 | Cancellation of the registration of the contract for pledge of patent right |
Date of cancellation: 20171011 Granted publication date: 20160217 Pledgee: Guilin SME credit Company Limited by Guarantee Pledgor: Guilin Huiang Biochemistry Pharmaceutical Co.,Ltd. Registration number: 2016450000012 |
|
PC01 | Cancellation of the registration of the contract for pledge of patent right | ||
PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: Novel photosensitizer monomer completely soluble in water, and preparation method and application thereof Effective date of registration: 20171013 Granted publication date: 20160217 Pledgee: Guilin SME credit Company Limited by Guarantee Pledgor: Guilin Huiang Biochemistry Pharmaceutical Co.,Ltd. Registration number: 2017450000010 |
|
PE01 | Entry into force of the registration of the contract for pledge of patent right | ||
PC01 | Cancellation of the registration of the contract for pledge of patent right |
Date of cancellation: 20181008 Granted publication date: 20160217 Pledgee: Guilin SME credit Company Limited by Guarantee Pledgor: Guilin Huiang Biochemistry Pharmaceutical Co.,Ltd. Registration number: 2017450000010 |
|
PC01 | Cancellation of the registration of the contract for pledge of patent right | ||
PE01 | Entry into force of the registration of the contract for pledge of patent right | ||
PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: Novel photosensitizer monomer completely soluble in water, and preparation method and application thereof Effective date of registration: 20181011 Granted publication date: 20160217 Pledgee: Financing Company limited by guarantee of small and micro enterprises in Guilin Pledgor: Guilin Huiang Biochemistry Pharmaceutical Co.,Ltd. Registration number: 2018450000028 |
|
PC01 | Cancellation of the registration of the contract for pledge of patent right |
Date of cancellation: 20191009 Granted publication date: 20160217 Pledgee: Financing Company limited by guarantee of small and micro enterprises in Guilin Pledgor: Guilin Huiang Biochemistry Pharmaceutical Co.,Ltd. Registration number: 2018450000028 |
|
PC01 | Cancellation of the registration of the contract for pledge of patent right | ||
PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: Novel photosensitizer monomer completely soluble in water, and preparation method and application thereof Effective date of registration: 20191011 Granted publication date: 20160217 Pledgee: Financing Company limited by guarantee of small and micro enterprises in Guilin Pledgor: Guilin Huiang Biochemistry Pharmaceutical Co.,Ltd. Registration number: Y2019450000017 |
|
PE01 | Entry into force of the registration of the contract for pledge of patent right | ||
PC01 | Cancellation of the registration of the contract for pledge of patent right |
Date of cancellation: 20220908 Granted publication date: 20160217 Pledgee: Financing Company limited by guarantee of small and micro enterprises in Guilin Pledgor: Guilin Huiang Biochemistry Pharmaceutical Co.,Ltd. Registration number: Y2019450000017 |
|
PC01 | Cancellation of the registration of the contract for pledge of patent right | ||
PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: A novel completely water-soluble photosensitizer monomer and its preparation method and application Effective date of registration: 20220913 Granted publication date: 20160217 Pledgee: Financing Company limited by guarantee of small and micro enterprises in Guilin Pledgor: Guilin Huiang Biochemistry Pharmaceutical Co.,Ltd. Registration number: Y2022450000149 |
|
PE01 | Entry into force of the registration of the contract for pledge of patent right | ||
PC01 | Cancellation of the registration of the contract for pledge of patent right |
Granted publication date: 20160217 Pledgee: Financing Company limited by guarantee of small and micro enterprises in Guilin Pledgor: Guilin Huiang Biochemistry Pharmaceutical Co.,Ltd. Registration number: Y2022450000149 |
|
PC01 | Cancellation of the registration of the contract for pledge of patent right | ||
PE01 | Entry into force of the registration of the contract for pledge of patent right | ||
PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: A novel fully water-soluble photosensitizer monomer and its preparation method and application Granted publication date: 20160217 Pledgee: Financing Company limited by guarantee of small and micro enterprises in Guilin Pledgor: Guilin Huiang Biochemistry Pharmaceutical Co.,Ltd. Registration number: Y2024450000066 |