C07D311/00

NOVEL HEAVY METAL ION-HEMATEIN-COMPLEXES USEFUL AS EX VIVO CONTRAST AGENT FOR A COMPUTED TOMOGRAPHY SCANNING OF A BIOLOGICAL SAMPLE, EX VIVO METHOD FOR INVESTIGATING A BIOLOGICAL SAMPLE, AND USE OF THE COMPLEXES
20200271554 · 2020-08-27 ·

The present invention relates to specific complexes comprising heavy metal ions having an atomic number of 23 or higher and 83 or lower (in particular Ag.sup.1+, Ba.sup.2+, Pb.sup.2+, Gd.sup.3+ and Bi.sup.3+) and one or more hematein ligand(s). In particular, the invention relates to the use of the complexes as ex vivo contrast agents for a computed tomography scanning of a biological sample. Moreover, the invention relates to specific ex vivo methods for investigating a biological sample by means of computed tomography scanning methods, wherein the method comprises staining the biological sample with a solution comprising one or more of the complex(es); or wherein the method comprises staining the biological sample with a staining solution comprising hematein, and separately contacting the biological sample with one or more staining solution(s) comprising one or more heavy metal ions having an atomic number of 23 or higher and 83 or lower (in particular Ag.sup.1+, Ba.sup.2+, Pb.sup.2+, Gd.sup.3+ and Bi.sup.3+).

NOVEL SALT COMPOUND, CHEMICALLY AMPLIFIED RESIST COMPOSITION, AND PATTERNING PROCESS

A novel salt having an amide bond in its anion structure is provided. A chemically amplified resist composition comprising the salt has advantages including minimal defects and improved values of sensitivity, LWR, MEF and CDU, when processed by lithography using high-energy radiation such as KrF excimer laser, ArF excimer laser, EB or EUV.

NOVEL SALT COMPOUND, CHEMICALLY AMPLIFIED RESIST COMPOSITION, AND PATTERNING PROCESS

A novel salt having an amide bond in its anion structure is provided. A chemically amplified resist composition comprising the salt has advantages including minimal defects and improved values of sensitivity, LWR, MEF and CDU, when processed by lithography using high-energy radiation such as KrF excimer laser, ArF excimer laser, EB or EUV.

Methods to separate cannabidiol and tetrahydrocannabinol

Various aspects of this patent document relate to methods to separate cannabidiol and tetrahydrocannabinol by adjusting their solubility in alcohol and water solutions.

Method of extracting one or more chemical extracts from a plant product

Disclosed is a method for extracting one or more chemical extracts from a plant product. The chemical extracts are purified and extracted by first separating at least a phytochemical bearing part of a plant product from one or more other portions of the plant product. A carrier oil is then heated at a target temperature to be used as the vehicle for extraction and then mixed with the at least a phytochemical bearing part while the target temperature is maintained. The process may be streamlined by having heating and mixing occur in a press device. The mixed carrier oil and the at least a phytochemical bearing part are then passed through the press device to produce an oil mixture. At least a chemical extract may be extracted from the oil mixture, and in some cases may be further purified by evaporation and/or centrifugation.

Cationic lipid

The present invention aims to provide a cationic lipid that can be used as a nucleic acid delivery carrier, a lipid membrane structure using a cationic lipid, a nucleic acid-introducing agent using a cationic lipid, and a method of achieving nucleic acid introduction by using a nucleic acid-introducing agent containing a cationic lipid. A lipid membrane structure containing a cationic lipid represented by the formula (1) ##STR00001##
wherein each symbol is as defined in the DESCRIPTION, is superior in the stability in blood and tumor accumulation property. A nucleic acid-introducing agent using the cationic lipid can achieve high nucleic acid delivery efficiency of nucleic acid to be delivered into the cytoplasm.

Cationic lipid

The present invention aims to provide a cationic lipid that can be used as a nucleic acid delivery carrier, a lipid membrane structure using a cationic lipid, a nucleic acid-introducing agent using a cationic lipid, and a method of achieving nucleic acid introduction by using a nucleic acid-introducing agent containing a cationic lipid. A lipid membrane structure containing a cationic lipid represented by the formula (1) ##STR00001##
wherein each symbol is as defined in the DESCRIPTION, is superior in the stability in blood and tumor accumulation property. A nucleic acid-introducing agent using the cationic lipid can achieve high nucleic acid delivery efficiency of nucleic acid to be delivered into the cytoplasm.

Medical compound

Provided is a medical compound including a synthetic flavone derivative, according to the formula (I) with allotment in position C-3 of a group as shown below: ##STR00001##
wherein at least two of R.sub.2-R.sub.6 are H, and the remaining are independently selected from: H, OH, R.sub.1, OR.sub.1, NO.sub.2, NH.sub.2, NHR.sub.1, F, Cl, Br, I, where R.sub.1 is a radical.

CYCLOHEXANE LIPIDOIDS FOR NUCLEIC ACID TRANSFECTION AND USE THEREOF

The present invention relates to a lipidoid of general formula I, wherein X is selected from C(?O)NH, C(?O)O, C(?S)O, C(?O)S, C(?S)S, C(?O)NHNH, CH.sub.2, O, OC(?O), S, SC(?O), NH, NHNH, NHC(?O), NHNHC(?O), C?C, CH?CH, a five-membered heterocycle containing at least 2 nitrogen atoms, CH.sub.2C(?O)NH, CH.sub.2C(?S)O, CH.sub.2C(?S)S, CH.sub.2C(?O)NHNH, N?CH, CH?N, NHN?CH, and CH?NNH; Y is alkylene C.sub.2-C.sub.10 chain; R.sup.1 is selected from alkyl C.sub.1-C.sub.46, alkenyl C.sub.2-C.sub.46, alkynyl C.sub.2-C.sub.46; Z is selected from H, OH, CH.sub.3, CH.sub.2OH, NH.sub.2, C(?O)NH.sub.2, CONH(CH.sub.2).sub.2OH, CON[(CH.sub.2).sub.2OH].sub.2, CONHCH(CH.sub.2OH).sub.2, CONHCH.sub.2CH(OH)CH.sub.2OH, CONH(CH.sub.2).sub.2C(?O)NH.sub.2, CON[CH.sub.2C(?O)NH.sub.2].sub.2, CONH(CH.sub.2).sub.2NHC(?O)NH.sub.2, CONH(CH.sub.2).sub.3N+(CH.sub.3).sub.2(CH.sub.2).sub.2SO.sub.3, CONH(CH.sub.2).sub.3N+(CH.sub.3).sub.2(CH.sub.2).sub.2COO.sup.?, COO(CH.sub.2).sub.2OP(?O)(O)O(CH.sub.2).sub.2N+(CH.sub.3).sub.3, N+(CH.sub.3).sub.2(CH.sub.2).sub.3SO.sub.3, N+(CH.sub.3).sub.2(CH.sub.2).sub.2COO.sup.?, formula (II), and formula (III), wherein R.sup.2 is independently selected from hydrogen and CH.sub.3; E is independently selected from O and S atoms; n is an integer within the range of from 1 to 5; and T is selected from XYN(R.sup.1).sub.2, C(?O)O(C.sub.1-C.sub.3 alkyl), C(?O)OCH.sub.2CH.sub.2OH, formula (IV), formula (V), formula (VI), C(?O)OH, CONH(CH.sub.2).sub.2OH, CON[(CH.sub.2).sub.2OH].sub.2, CONHCH(CH.sub.2OH).sub.2, CONH(CH.sub.2).sub.2C(?O)NH.sub.2, CON[CH.sub.2C(?O)NH.sub.2].sub.2, CONHCH[C(?O)NH.sub.2].sub.2, CONH(CH.sub.2).sub.2NHC(?O)NH.sub.2, C(?O)NH.sub.2, CONH(CH.sub.2).sub.3N+(CH.sub.3).sub.2(CH.sub.2).sub.2SO.sub.3, CONH(CH.sub.2).sub.3N+(CH.sub.3).sub.2(CH.sub.2).sub.2COO.sup.?, NH.sub.2, NHC(?O)CH.sub.3, COO(CH.sub.2).sub.2OP(?O)(O)O(CH.sub.2).sub.2N+(CH.sub.3).sub.3, OH, O(C.sub.1-C.sub.3 alkyl), NHC(?O)NH(CH.sub.3), NHC(?S)N(CH.sub.3).sub.2, NHC(?S)NH(CH.sub.3), NHC(?NCN)NH.sub.2, NHC(?NCN)NH(CH.sub.3), NHC(?NCN)N(CH.sub.3).sub.2, NHC[?NS(?O).sub.2NH.sub.2]NH.sub.2, N+(CH.sub.3).sub.2(CH.sub.2).sub.3SO.sub.3, N+(CH.sub.3).sub.2(CH.sub.2).sub.2COO.sup.?, wherein R.sup.2, E and n are as defined above; and/or if Z is OH or CH.sub.2OH, and T is C(?O)OH, then Z together with T and three carbon atoms between them may form a cyclic lactone containing 4 to 5 carbon atoms; and pharmaceutically acceptable salts, addition salts and solvates thereof. This lipidoid is useful as a transfection agent. The invention further describes transfection reagents, transfection particles containing this lipidoid, and their use.

##STR00001##

CYCLOHEXANE LIPIDOIDS FOR NUCLEIC ACID TRANSFECTION AND USE THEREOF

The present invention relates to a lipidoid of general formula I, wherein X is selected from C(?O)NH, C(?O)O, C(?S)O, C(?O)S, C(?S)S, C(?O)NHNH, CH.sub.2, O, OC(?O), S, SC(?O), NH, NHNH, NHC(?O), NHNHC(?O), C?C, CH?CH, a five-membered heterocycle containing at least 2 nitrogen atoms, CH.sub.2C(?O)NH, CH.sub.2C(?S)O, CH.sub.2C(?S)S, CH.sub.2C(?O)NHNH, N?CH, CH?N, NHN?CH, and CH?NNH; Y is alkylene C.sub.2-C.sub.10 chain; R.sup.1 is selected from alkyl C.sub.1-C.sub.46, alkenyl C.sub.2-C.sub.46, alkynyl C.sub.2-C.sub.46; Z is selected from H, OH, CH.sub.3, CH.sub.2OH, NH.sub.2, C(?O)NH.sub.2, CONH(CH.sub.2).sub.2OH, CON[(CH.sub.2).sub.2OH].sub.2, CONHCH(CH.sub.2OH).sub.2, CONHCH.sub.2CH(OH)CH.sub.2OH, CONH(CH.sub.2).sub.2C(?O)NH.sub.2, CON[CH.sub.2C(?O)NH.sub.2].sub.2, CONH(CH.sub.2).sub.2NHC(?O)NH.sub.2, CONH(CH.sub.2).sub.3N+(CH.sub.3).sub.2(CH.sub.2).sub.2SO.sub.3, CONH(CH.sub.2).sub.3N+(CH.sub.3).sub.2(CH.sub.2).sub.2COO.sup.?, COO(CH.sub.2).sub.2OP(?O)(O)O(CH.sub.2).sub.2N+(CH.sub.3).sub.3, N+(CH.sub.3).sub.2(CH.sub.2).sub.3SO.sub.3, N+(CH.sub.3).sub.2(CH.sub.2).sub.2COO.sup.?, formula (II), and formula (III), wherein R.sup.2 is independently selected from hydrogen and CH.sub.3; E is independently selected from O and S atoms; n is an integer within the range of from 1 to 5; and T is selected from XYN(R.sup.1).sub.2, C(?O)O(C.sub.1-C.sub.3 alkyl), C(?O)OCH.sub.2CH.sub.2OH, formula (IV), formula (V), formula (VI), C(?O)OH, CONH(CH.sub.2).sub.2OH, CON[(CH.sub.2).sub.2OH].sub.2, CONHCH(CH.sub.2OH).sub.2, CONH(CH.sub.2).sub.2C(?O)NH.sub.2, CON[CH.sub.2C(?O)NH.sub.2].sub.2, CONHCH[C(?O)NH.sub.2].sub.2, CONH(CH.sub.2).sub.2NHC(?O)NH.sub.2, C(?O)NH.sub.2, CONH(CH.sub.2).sub.3N+(CH.sub.3).sub.2(CH.sub.2).sub.2SO.sub.3, CONH(CH.sub.2).sub.3N+(CH.sub.3).sub.2(CH.sub.2).sub.2COO.sup.?, NH.sub.2, NHC(?O)CH.sub.3, COO(CH.sub.2).sub.2OP(?O)(O)O(CH.sub.2).sub.2N+(CH.sub.3).sub.3, OH, O(C.sub.1-C.sub.3 alkyl), NHC(?O)NH(CH.sub.3), NHC(?S)N(CH.sub.3).sub.2, NHC(?S)NH(CH.sub.3), NHC(?NCN)NH.sub.2, NHC(?NCN)NH(CH.sub.3), NHC(?NCN)N(CH.sub.3).sub.2, NHC[?NS(?O).sub.2NH.sub.2]NH.sub.2, N+(CH.sub.3).sub.2(CH.sub.2).sub.3SO.sub.3, N+(CH.sub.3).sub.2(CH.sub.2).sub.2COO.sup.?, wherein R.sup.2, E and n are as defined above; and/or if Z is OH or CH.sub.2OH, and T is C(?O)OH, then Z together with T and three carbon atoms between them may form a cyclic lactone containing 4 to 5 carbon atoms; and pharmaceutically acceptable salts, addition salts and solvates thereof. This lipidoid is useful as a transfection agent. The invention further describes transfection reagents, transfection particles containing this lipidoid, and their use.

##STR00001##