Novel tetrapyrrole compound and application thereof
What is Al technical title?
Al technical title is built by PatSnap Al team. It summarizes the technical point description of the patent document.
A tetrapyrrole compound and compound technology, applied in the field of photosensitive drugs and photodynamic therapy, can solve the problems of unstable structure, strong skin phototoxicity, and high cost, and achieve the effect of low skin phototoxic side effects and significant photodynamic activity
Pending Publication Date: 2021-12-07
SHANGHAI XIANHUI MEDICAL TECH
View PDF12 Cites 1 Cited by
Summary
Abstract
Description
Claims
Application Information
AI Technical Summary
This helps you quickly interpret patents by identifying the three key elements:
Problems solved by technology
Method used
Benefits of technology
Problems solved by technology
[0010] In order to overcome the defects of complex composition, unstable structure, difficult preparation, high cost and strong skin phototoxicity in existing photosensitive drugs, the present invention introduces two An alkyl grou...
Method used
the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more
Image
Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
Click on the blue label to locate the original text in one second.
Reading with bidirectional positioning of images and text.
Smart Image
Examples
Experimental program
Comparison scheme
Effect test
Embodiment 1
[0075] 5,15-bis[4-(N,N-dicarboxymethyl)aminophenyl]porphine (I 1 ) preparation method
[0076]
[0077] Compound I 1a (2.7mmol) and dipyrromethane (0.395g, 2.7mmol) were dissolved in DCM (500mL), and trifluoroacetic acid (0.12mL, 1.7mmol) was added dropwise under nitrogen protection, and the reaction was stirred at room temperature for 3h. Dichlorodicyanobenzoquinone DDQ (0.735 g, 3.24 mmol) and triethylamine (4 mL) were added, and the stirring reaction was continued for 3 h. The solvent was distilled off under reduced pressure, and the obtained residue was separated and purified by column chromatography (MeOH / DCM=1 / 200) to obtain a purple solid I 1b (1.2mmol), yield 44.3%. 1 HNMR (400MHz, CDCl 3 ): δppm 10.31(s, 2H), 9.41(d, J=3.7Hz, 4H), 9.18(d, J=3.5Hz, 4H), 8.17(d, J=8.4Hz, 4H), 7.08(d, J=8.8Hz, 4H), 4.48(s, 8H), 4.41(q, J=7.3Hz, 8H), 1.44(t, J=7.2Hz, 12H), -3.02(s, 2H).MS(MALDI -TOF)m / z[M+H] + ,837.3.
[0078] Compound I 1b (0.50mmol) dissolved in THF / MeOH (50...
Embodiment 2
[0080] 5,15-bis[4-(N,N-dicarboxyethyl)aminophenyl]porphine (I 2 ) preparation method
[0081]
[0082] Compound I 1 Similar preparation method, obtained compound I 2 , yield 31.8%. 1 H NMR (400MHz, DMSO-d 6 ): δppm 12.27(s, 4H), 10.46(s, 2H), 9.56(d, J=4.2Hz, 4H), 9.20(d, J=4.4Hz, 4H), 8.16(d, J=8.0Hz, 4H), 7.35(d, J=8.0Hz, 4H), 3.62(d, J=8.6Hz, 8H), 2.60(t, J=7.3Hz, 8H), -2.87(s, 2H). HRMS(MALDI):m / z calcd for C 44 h 41 N 6 o 8 [M+H] + , 781.2902; found, 781.2805.
Embodiment 3
[0084] 5,15-bis[4-(N,N-dicarboxy-n-propyl)aminophenyl]porphine (I 3 ) preparation method
[0085]
[0086] Compound I 1 Similar preparation method, obtained compound I 3 , yield 29.8%. 1 H NMR (400MHz, DMSO-d 6 ): δppm 12.25(s, 4H), 10.55(s, 2H), 9.61(d, J=4.4Hz, 4H), 9.16(d, J=4.4Hz, 4H), 8.10(d, J=8.0Hz, 4H), 7.27(d, J=8.0Hz, 4H), 3.59(d, J=9.0Hz, 8H), 2.48(t, J=7.2Hz, 8H), 2.46-2.00(m, 8H), -2.99 (s,2H). 13 C NMR (100MHz, DMSO-d 6 ): δppm 174.91, 147.60, 144.69, 136.66, 132.66, 131.33, 111.13, 105.86, 50.15, 31.50, 22.82. HRMS (MALDI): m / z calcdfor C 48 h 49 N 6 o 8 [M+H] + , 837.3506; found, 837.3569.
the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more
PUM
Login to view more
Abstract
The invention relates to a novel water-soluble intermediate di (disubstituted amino) phenyl porphin tetrapyrrole compound which is good in hydrophilicity, easy to prepare into an injection and simple and feasible in preparation process, and a preparation method of the tetrapyrrole compound shown in the description, wherein X is H, Cl, Br, or I; R is a meta-position or para-position group, and R is -N (R1) 2; R1 is -(CH2)nCOOH, and n is equal to 1-6; and R2 is 2H or Zn. The invention relates to the field of photosensitive drugs and photodynamic therapy, in particular to a novel intermediate di (disubstituted amino) phenyl porphin tetrapyrrole compound which is good in hydrophilicity and easy to prepare into injection, a preparation method of the intermediate di (disubstituted amino) phenyl porphin tetrapyrrole compound and application of the intermediate di (disubstituted amino) phenyl porphin tetrapyrrole compound in the field of medicine. The intermediate di (disubstituted amino) phenyl porphin photosensitizer prepared by the invention has remarkable photodynamic activity and low skin light toxic and side effects, and can be used as a drug for photodynamic diagnosis and treatment of diseases such as tumors, retina macular degeneration, actinic keratosis, nevus flammeus and condyloma acuminata.
Description
technical field [0001] The invention relates to the field of photosensitizing drugs and photodynamic therapy, in particular to a class of intermediary di(disubstituted amino)phenylporphine tetrapyrrole compounds with stable structure, simple and convenient preparation method, good hydrophilicity and easy preparation into injections and its Applications in the field of medicine. Background technique [0002] Photodynamic therapy (PDT) is a novel method for the treatment of tumors, macular degeneration, port wine stains and other diseases. After the photosensitizer enters the human body, under the irradiation of external light of a certain wavelength, it changes from the ground state to the excited state, generating free radicals and reactive oxygen species (ROS), which can cause direct damage to the lesion cells, and can also damage the blood vessels around the lesion. , thus blocking the supply of nutrients to the lesion and causing indirect damage. Compared with conventio...
Claims
the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more
Application Information
Patent Timeline
Application Date:The date an application was filed.
Publication Date:The date a patent or application was officially published.
First Publication Date:The earliest publication date of a patent with the same application number.
Issue Date:Publication date of the patent grant document.
PCT Entry Date:The Entry date of PCT National Phase.
Estimated Expiry Date:The statutory expiry date of a patent right according to the Patent Law, and it is the longest term of protection that the patent right can achieve without the termination of the patent right due to other reasons(Term extension factor has been taken into account ).
Invalid Date:Actual expiry date is based on effective date or publication date of legal transaction data of invalid patent.
Login to view more 
Login to view more