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Heteroannelated anthraquinone derivatives and the synthesis method thereof


Title: Heteroannelated anthraquinone derivatives and the synthesis method thereof.
Abstract: wherein R1 is a substituent being one selected from a group consisting of i) a first substituent being one selected from a group consisting of a hydryl group, an amino group, a nitro group, a hydroxyl group and a cyan group, ii) a second substituent being one selected from a group consisting of (CH2)nX, a straight (CH2)n alkyl group, a (CH2)n alkoxyl group, a branched (CH2)n alkyl group, a C3˜C12nephthenic group, and a C3˜C12 cyclic alkoxyl group, wherein 1=n=12, and X is a halogen, iii) a third substituent being one selected from a group consisting of a straight C1˜C8 alkyl group with a double-bond, a C1˜C8 alkoxyl group with a double-bond, a branched C1˜C8 alkyl group with a double-bond and a C3˜C8 nephthenic group with a double-bond, and iv) a fourth substituent of a C5˜C12 heterocyclic group. A heteroannelated anthraquinone derivative compound is provided. The heteroannelated anthraquinone derivative compound is represented by a formula (I): ...

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USPTO Applicaton #: #20090253707 - Class: $ApplicationNatlClass (USPTO) -
Inventors: Hsu-shan Huang



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The Patent Description & Claims data below is from USPTO Patent Application 20090253707, Heteroannelated anthraquinone derivatives and the synthesis method thereof.

FIELD OF THE INVENTION

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The present invention relates to heteroannelated anthraquinone derivatives for inhibiting a proliferation activity of a cancer cell, and more particularly to a series of heteroannelated anthraquinone derivatives and the synthesis method thereof.

BACKGROUND OF THE INVENTION

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In normal somatic cells, the telomere, which is located at the end of a chromosome, gets shortened at each time of cell mitosis. When the telomere is shortened to some level, the cell will lose the ability of replication and go into apoptosis stage. Telomerase, which is a ribonucleoprotein, acts on the telomere in a eukaryocyte, so as to prolong or maintain the length of the telomere. A telomerase mainly includes two portions; one is a protein sub-unit with activity of reverse transcription, i.e. the human telomerase reverse transcriptase (hTERT), and the other one is an RNA template for synthesizing repeated sequences of the telomerase, i.e. the human telomerase RNA component (hTR), wherein the RNA template includes the single RNA sequence, -AAUCCC, which is complementary to the telomerase sequence. Telomerase activity is rarely detected in normal human somatic cells, but is usually detected in the cells that keep proliferating, such as hematopoietic cells, embryogenic cells, stem cells, etc. It is estimated that about 85-90% of human tumor cells have telomerase activity, and that is the reason why tumor cells do not go into apoptosis like a normal cell and can keep proliferating (Urquidi et al., Annu. Rev. Med. 2000, 51, 65-79). Reductions in hTERT mRNA expression level and telomerase activity are observed during the processes of cell going aged or immortalized (Bestilny et al., Cancer Res. 1996, 56, 3796-802). Furthermore, the telomerase activity of a somatic cell that should not express the telomerase activity could be reproduced by introduction of the hTERT cDNA thereinto for a high level expression of telomerase activity (Bodnar et al., Science. 1998, 279, 349-52).

The telomere at chromosome ends of eukaryotic cells is guanine-rich. In normal physiological conditions, the single strand DNA of the telomere spontaneously forms a G-quadruplex structure. The G-quadruplex structure includes two portions, wherein one is a small loop composed of TTA, and the other one is a guanine-tetrad composed of four guanines formed by cyclic hydrogen bonds. In order to inhibit the differentiation of tumor cells, an alternative besides the direct inhibition to telomerase activity is to stabilize the G-quadruplex structure for inhibiting its reaction with the complementary single strand RNA (AAUCCC), so as to prevent the telomerase from extending the telomere. Chromosome replications of tumor cells may be inhibited by the mentioned method, so as to achieve the anti-caner effect directly or indirectly (Smogorzewska et al., Annu. Rev. Biochem. 2004, 73, 177-208).

It is observed in current studies that anthraquinone can stabilize the G-quadruplex structure for its formula with plane tri-cyclic structure. According to the researches to the quindoline derivatives (10H-indolo[3,2-b]quinoline) with tetra-cyclic structure, berberin with non-plane polycyclic structure and the analogs synthesized therefrom, it is known that the aromatic groups of the mentioned compounds play an important role in the bonding to the G-quardruplex structure. Over-expressions of known oncogenes usually induce cancers and are associated with many cell proliferation disorders, such as chronic lymphocytic leukemia, esophagus cancer, myeloma, etc. In additions, those genes also participate in many pathological and physiological processes. Many experiments have proved that over-expressions of tumor suppressor genes play important role in the prevention and treatment of tumors. Therefore, the research and development of the drugs for curing cell proliferation disorders can be applied in the cure of human cancers, just like the disclosures of Canadian Patent No. 2,428,206.

Although it has been published that a heteroannelated anthraquinone derivative can be synthesized by an acylation reaction of 1,2-diaminoanthraquinone to obtain a bis-substituent derivative, followed by a consensation reaction. However, this method only discloses the substituent of aromatic groups, and has a poor production rate (Peng et al., J. Org. Chem. 2005, 70, 10524-31).

Based on the above, the present invention provides heteroannelated anthraquinone derivatives and the synthesis method thereof, which is accomplished by preserving the chromophore group with plane tri-cyclic structure and the carbonyl groups at 9 and 10, which have better binding ability, then changing the tri-cyclic structure into tetra-cyclic structure and adding various side chains derived from different modified substituents, so as to synthesize a series of heteroannelated anthraquinone derivatives.

SUMMARY

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OF THE INVENTION

The present invention provides a series of heteroannelated anthraquinone derivatives for inhibiting the proliferation activity of cancer cells, which facilitate the study and application regarding cancer cells.

In accordance with the first aspect of the present invention, a heteroannelated anthraquinone derivative compound is provided. The compound is represented by a formula (I):

wherein R1 is a substituent being one selected from a group consisting of i) a first substituent being one selected from a group consisting of a hydryl group, an amino group, a nitro group, a hydroxyl group and a cyan group, ii) a second substituent being one selected from a group consisting of (CH2)nX, a straight (CH2)n alkyl group, a (CH2)n alkoxyl group, a branched (CH2)n alkyl group, a C3˜C12nephthenic group, and a C3˜C12 cyclic alkoxyl group, wherein 1=n=12, and X is a halogen, iii) a third substituent being one selected from a group consisting of a straight C1˜C8 alkyl group with a double-bond, a C1˜C8 alkoxyl group with a double-bond, a branched C1˜C8 alkyl group with a double-bond and a C3˜C8 nephthenic group with a double-bond, and iv) a fourth substituent of a C5˜C12 heterocyclic group, wherein one of the nephthenic group and the heterocyclic group further has at least one of an ortho-substitution, a meta-substitution and a para-substitution, and comprises at least a fifth substituent for any of the substitutions being one selected from a group consisting of an alkyl group with a C1˜-C3 substituent branch, an amino group, a nitro group, a hydroxyl group and a cyan group, a C1˜C5 alkyl group, a halogen substituted C1˜C5 alkyl group, a C1˜C5 alkoxyl group, a halogen substituted C1˜C5 alkoxyl group, a C1˜C5 cyclic alkoxyl group, and a halogen substituted C1˜C5 cyclic alkoxyl group.

Preferably, the halogen is one selected from a group consisting of a fluorine, a chlorine, a bromine and an iodine.

Preferably, the second substituent is one selected from a group consisting of a methyl group, an ethyl group, a propyl group, a butyl group, an isobutyl group, a pentyl group, an isopentyl group, a cyclopentyl group, a heptyl group, an isoheptyl group, a cycloheptyl group, an octyl group, an isooctyl group, a cyclooctyl group, a straight alkyl group with a branch substituted by a straight C1˜C5 alkyl group, a nephthenic group with a branch substituted by a straight C1˜C5 alkyl group, alkoxyl derivatives of the mentioned alkyl groups, and halogenated derivatives of the mentioned alkyl groups.

Preferably, the third substituent is one selected from a group consisting of a vinyl group, a propenyl group, a butenyl group, an isobutenyl group, a pentenyl group, an isopentenyl group, a cyclopentenyl group, a hexenyl group, a cyclohexenyl group, a heptenyl group, an cycloheptenyl group, a straight alkyl group with a branch substituted by a straight C1˜C3 alkyl group, a nephthenic group with a branch substituted by a straight C1˜C3 alkyl group, alkoxyl derivatives of the mentioned groups, and halogenated derivatives of the mentioned groups.

Preferably, the heteroannelated anthraquinone derivative compound is used as an effective component together with an excipient to provide a pharmaceutic composition for inhibiting one selected from a group consisting of a growth of a cancer cell, a disease of cell proliferation, and a growth of cell telomere.

In accordance with the second aspect of the present invention, a heteroannelated anthraquinone derivative compound is provided. The compound is represented by a formula (II):

Preferably, the heteroannelated anthraquinone derivative compound is used as an effective component together with an excipient to provide a pharmaceutic composition for inhibiting one selected from a group consisting of a growth of a cancer cell, a disease of cell proliferation, and a growth of cell telomere.

In accordance with the third aspect of the present invention, a heteroannelated anthraquinone derivative compound is provided. The compound is represented by a formula (III):

wherein either one of R2 and R3 is one of i) a first substituent being one of a hydryl group and a sulfuryl-group, and ii) a second substituent being one selected from a group consisting of a C1˜C8 alkyl group, a C1˜C8 alkoxyl group, a C3˜C8 nephthenic group, and a C3˜C8 cyclic alkoxyl group, a straight alkyl group with a branch substitutent, a nephthenic group with a branch substitutent by a straight C1˜C5 alkyl group and halogenated derivatives of the mentioned substitent groups.

Preferably, the second substituent is one selected from a group consisting of a methyl group, an ethyl group, a propyl group, a butyl group, an isobutyl group, a pentyl group, an isopentyl group, a cyclopentyl group, a heptyl group, an isoheptyl group, a cycloheptyl group, an octyl group, an isooctyl group, a cyclooctyl group, a phenyl group, a benzyl group, a phenethyl group, a straight alkyl group with a branch substituted by a straight C1˜C3 alkyl group, a nephthenic group with a branch substituted by a straight C1˜C3 alkyl group, alkoxyl derivatives of the mentioned substituent groups, and halogenated derivatives of the mentioned substituent groups.

Preferably, the heteroannelated anthraquinone derivative is used as an effective component together with an excipient to provide a pharmaceutic composition for inhibiting one selected from a group consisting of a growth of a cancer cell, a disease of cell proliferation, and a growth of cell telomere.

In accordance with the fourth aspect of the present invention, a heteroannelated anthraquinone derivative compound is provided. The compound is represented by a formula (IV):

wherein R4 is one selected from a group consisting of a hydryl group, a C1˜C4 alkyl group, a C1˜C4 alkoxyl group, a C1˜C4 ketone group, a straight alkyl group with a branch substituted by a straight C1˜C3 alkyl group, a halogen substituted C1˜C4 alkyl group, and a C1˜C4 alkoxyl group.

Preferably, A compound as claimed in claim 12, being used as an effective component together with an excipient to provide a pharmaceutic composition for inhibiting one selected from a group consisting of a growth of a cancer cell, a disease of cell proliferation, and a growth of cell telomere.

In accordance with the fifth aspect of the present invention, a method for manufacturing a compound having the formula (I) is provided. The method includes steps of a) dissolving a diaminoanthraquinone in a dimethylformamide solution for forming a solution A, b)adding and dissolving a chloroacetyl chloride in the solution A for forming a solution B, c) mixing and reacting the solution B by a reverse flow method, and then transferring the solution B into an icy water for forming a solution C, d) filtering the solution C for obtaining a precipitate, and e) washing the precipitate by using an ethanol for obtaining the compound of the formula (I).

In accordance with the sixth aspect of the present invention, a method for manufacturing a compound having the formula (I) is provided. The method includes steps of a) dissolving a diaminoanthraquinone in a dimethylformamide solution for forming a solution A, b) adding and dissolving a reagent in the solution A for forming a solution B, wherein the reagent is one of a benzaldehyde and a carbon disulfide, c) catalyzing a reaction of the solution B by adding a concentrated sulfuric acid thereinto, and then transferring the solution B into an ice water for forming a solution C, d) filtering the solution C for obtaining a precipitate, and e) washing the precipitate by using an ethanol for obtaining the compound of the formula (I), wherein when the reagent is the carbon disulfide, a triethylamine is further added into the solution B before the step c).

In accordance with the seventh aspect of the present invention, a method for manufacturing a compound having the formula (III) is provided. The method includes steps of a) dissolving a diaminoanthraquinone in an acetone for forming a solution A, b) adding a concentrated sulfuric acid into the solution A for forming a solution B, c) transferring the solution B into a potassium carbonate column for obtaining a solution C, and d) using a methanol to crystallize the compound of the formula (III) in the solution C.

Preferably, the step b) is performed in a room temperature.

In accordance with the eighth aspect of the present invention, a method for manufacturing a compound having the formula (IV) is provided. The method includes steps of a) dissolving a diaminoanthraquinone in a dimethylformamide solution for forming a solution A, b) adding a glyoxal ethanol solution into the solution A for forming a solution B, c) reacting the solution B by a reverse flow reaction, d) filtering the solution B for obtaining a precipitate, and e) washing the precipitate by using a hot alcohol and a dichloromethane for separating out the compound of the formula (IV).

Alternatively, in some steps of the above-mentioned methods, the production rate will increase if the solvents used for dissolving the diaminoanthraquinone contain less water. In the purification steps for the products, alcohol could be used for crystallization; alternatively, hot alcohol could be used for washing the products. The products with high solubility could be dissolved in alcohol before crystallization. The products with low solubility need to be washed by hot alcohol to wash out initial material or impurities and by-products generated in the reaction. Compared with recrystallization, although parts of products would be lost in the washing steps, it would be easier to obtain the purified products.

The compound provided in the present invention could be supplied with excipients, carriers or diluent, such starch or binder like carboxymethyl cellulose (CMC), so as to prepare granulated pill, tablet, or capsule. Alternatively, the compound could be dissolved in phosphate buffer for adjusting the pH thereof, so as to prepare injection. The compound could be supplied with penetration enhancer, so as to prepare absorbate by skin.

Additional objects and advantages of the invention will be set forth in the following descriptions.

DETAILED DESCRIPTION

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OF THE PREFERRED EMBODIMENT

The present invention will now be described more specifically with the experiment results of the following embodiments. It is to be noted that the following descriptions of preferred embodiments of this invention are presented herein for the purposes of illustration and description only; it is not intended to be exhaustive or to be limited to the precise form disclosed.

Concretely speaking, the method for manufacturing the heteroannelated anthraquinone derivative includes cyclization and condensation reactions.

Embodiment 1 (2-Methyl-1(3)H-anthra[1,2-d]imidazole-6,11-dione, No. 2)

1,2-Diaminoanthraquinone (1.19 g, 5 mmol) is dissolved in 30 mL of N,N-dimethylformamide, and chloroacetyl chloride (0.5 mL, 6 mmol) is added thereinto. After ten hours of mixing and reacting by a reverse flow, the mixture is transferred into 200 mL of icy water. After filtering, the precipitate is collected and washed by hot alcohol, so as to obtain the black compound No. 2.

The compound No. 2 has the following characterstics: MW 262.0724 (C16H9N2O2); Rf: 0.79 (ethyl acetate: dichloromethane=1:4); IR (KBr) cm−1: 1667 (CO); EI-MS m/z: 262 (M+, 100%); 1H-NMR (300 MHz, DMSO-d6) d (ppm): 2.72 (3H, s,—CH3), 7.75-7.82 (2H, m, Ar—H7,10), 7.93 (1H, d, J=8.4 Hz, Ar—H5), 8.13 (1H, d, J=8.4 Hz, Ar—H4), 8.19-8.23 (1H, m, Ar—H8,9), 11.01 (1H, br, —NH); and 13C-NMR (75 MHz, DMSO-d6) d (ppm): 23.89, 120.23, 121.22, 125.29, 126.19, 126.75, 127.19, 128.17, 128.87, 132.98, 134.18, 134.42, 148.22, 158.09, 182.43 (CO), 185.13 (CO).

Embodiment 2 (2-Chloroacetyl-1(3)H-anthra[1,2-d]imidazole-6,11-dione, No. 3)

Except controlling the reacting temperature in 50-60° C., all steps are identical with the steps for manufacturing the compound No. 2, and the yellowish brown compound No. 3 can be obtained.

The compound No. 3 has the following characterstics: MW 296.0353 (C16H9N2O2Cl); Rf: 0.5 (ethyl acetate: dichloromethane=1:4); IR (KBr) cm−1: 3359(NH), 1660 (CO); HRMS (ESI-TOF) m/z: calcd for C16H10N2O2Cl+ [M+H]+: 297.0425, found: 297.0426; 1H-NMR (300 MHz, CDCl3) d (ppm): 4.92 (2H, s, —CH2Cl), 7.80-7.83 (2H, m, Ar—H7,10), 8.08 (1H, d, J=8.4 Hz, Ar—H5), 8.24(1H, d, J=8.4 Hz, Ar—H4), d8.26-8.35(2H, m, Ar—H8,9), d11.21(1H, br, —NH); and 13C-NMR (75 MHz, DMSO) d (ppm): 37.80, 119.35, 121.27, 125.95, 126.83, 127.40, 129.06, 132.35, 133.47, 133.64, 134.88, 135.10, 148.89, 156.93, 183.04 (CO), 183.83 (CO).

Embodiment 3 (2-Ethyl-1(3)H-anthra[1,2-d]imidazole-6,11-dione, No. 4)

1,2-Diaminoanthraquinone (1.19 g, 5 mmol) was dissolved in dimethylformamide (30 mL), and propionaldehyde (0.29 g, 5 mmol) is added thereinto. Concentrated sulfuric acid (0.1 mL) is added thereinto for catalyzation. After mixing and reacting at room temperature for one hour, the reacted mixture is transferred into 200 mL of icy water and is extracted by using dichloromethane. The extract is dried, and crystallized by using alcholo, so as to obtain the brown compound No. 4.

The compound No. 4 has the following characterstics: MW 276.0899 (C17H12N2O2); Rf: 0.75 (ethyl acetate: dichloromethane=1:4); IR (KBr) cm−1: 1669 (CO); HRMS (ESI-TOF) m/z: calcd for C17H13N2O2+ [M+H]+: 277.0971, found: 277.0975 calcd for C17H12N2O2Na+ [M+Na]+: 299.0971, found: 299.0794; 1H-NMR (300 MHz, CDCl3) d (ppm): 1.51 (3H, t, J=7.5 Hz, —CH3), 3.05 (2H, q, J=7.5 Hz, —CH2—), 7.73-7.81 (2H, m, Ar—H7,10), 7.99 (1H, d, J=8.4 Hz, Ar—H5), d8.16(1H, d, J=8.4 Hz, Ar—H4), d8.21-8.23(1H, m, Ar—H9), d8.27-8.31(1H, m, Ar—H8), d10.85(1H, br, —NH); and 13C-NMR (75 MHz, CDCl3) d (ppm): 11.87, 22.89, 117.74, 121.50, 125.21, 126.47, 127.55, 128.21, 132.72, 133.24, 133.72, 133.99, 134.37, 148.90, 161.64, 182.81 (CO), 185.15 (CO).

Embodiment 4 (2-Isopropyl-1(3)H-anthra[1,2-d]imidazole-6,11-dione, No. 5)

All steps for manufacturing the yellow compound No. 5 are identical with the steps of Embodiment 3, except that propionaldehyde is substituted by isobutyraldehyde (0.41 g, 5 mmol).

The compound No. 5 has the following characterstics: MW 290.1055 (C18H14N2O2); Rf: 0.7 (ethyl acetate: dichloromethane=1:4); IR (KBr) cm−1: 3445 (NH), 1662 (CO); HRMS (ESI-TOF) m/z: calcd for C18H15N2O2+ [M+H]+: 291.1120, found: 291.1123; 1H-NMR (300 MHz, CDCl3) d (ppm): d1.56(6H, d, J=6.6 Hz, —CH3), d3.40(1H, sp, J=6.6 Hz, —CH—), d7.78-7.85(2H, m, Ar—H7,10), d8.11(1H, d, J=8.4 Hz, Ar—H5), d8.23(1H, d, J=8.4 Hz, Ar—H4), d8.25-8.36(2H, m, Ar—H8,9), d10.88(1H, s, —NH); and 13C-NMR (75 MHz, CDCl3) d (ppm): 21.15, 29.21, 117.66, 121.36, 125.21, 126.32, 127.42, 128.05, 132.49, 133.10, 133.61, 133.86, 134.24, 148.71, 165.35, 181.05(CO), 182.73(CO).

Embodiment 5 (2-Butyl-1(3)H-anthra[1,2-d]imidazole-6,11-dione, No. 6)

All steps for manufacturing the brown compound No. 6 are identical with the steps of Embodiment 3, except that propionaldehyde is substituted by pentanal (0.45 g, 5 mmol).

The compound No. 6 has the following characterstics: MW 304.1212 (C19H16N2O2); Rf: 0.65 (ethyl acetate: dichloromethane=1:4); IR (KBr) cm−1: 1669 (CO); HRMS (ESI-TOF) m/z: calcd for C19H17N2O2+ [M+H]+: 305.1276, found: 305.1282 calcd for C19H15N2O2− [M-H]−: 303.1131, found: 303.1135; 1H-NMR (300 MHz, CDCl3) d (ppm): d1.00(3H, t, J=7.2 Hz, —CH3), d1.50(2H, sx, J=7.5 Hz, —CH2—), d1.93(2H, qt, J=7.8 Hz —CH2—), d3.04(2H, t, J=7.5 Hz, —CH2—), d7.62-7.83(2H, m, Ar—H7,10), d8.03(1H, d, J=8.4 Hz, Ar—H5), d8.20, 1H, d, J=8.1 Hz, Ar—H4), d8.24-8.35(2H, m, Ar—H8,9) d10.83(1H, s, —NH); and 13C-NMR (75 MHz, CDCl3) d (ppm): 12.98, 21.78, 28.60, 29.27, 117.32, 121.07, 124.64, 125.98, 127.08, 127.83, 132.17, 132.84, 133.20, 133.61, 133.86, 148.25, 160.29, 182.31(CO), 184.78(CO).

Embodiment 6 (2-sec-Butyl-1(3)H-anthra[1,2-d]imidazole-6,11-dione, No. 7)

All steps for manufacturing the yellow compound No. 7 are identical with the steps of Embodiment 3, except that propionaldehyde is substituted by methylbutyraldehyde (0.46 g, 5 mmol).

The compound No. 7 has the following characterstics: MW 304.1212 (C19H16N2O2); Rf: 0.57 (ethyl acetate: dichloromethane=1:4); IR (KBr) cm−1: 1665 (CO); HRMS (ESI-TOF) m/z: calcd for C19H17N2O2+ [M+H]+: 305.1276, found: 305.1280 calcd for C19H15N2O2− [M−H]−: 303.1131, found: 303.1137; 1H-NMR (300 MHz, CDCl3) d (ppm): d1.00(3H, t, J=7.2 Hz, —CH3), d1.52(3H, d, J=6.9 Hz , —CH3), d1.82-2.02(2H, m, —CH2—), d3.04(1H, sx, J=7.2 Hz, —CH—), d7.62-7.83(2H, m, Ar—H7,10), d8.03(1H, d, J=8.4 Hz, Ar—H5), d8.20(1H, d, J=8.1 Hz, Ar—H4), d8.24-8.35(2H, m, Ar—H8,9), d10.83(1H, s, —NH); and 13C-NMR (75 MHz, CDCl3) d (ppm): 11.09, 18.09, 28.40, 35.71, 117.39, 121.07, 124.75, 125.95, 127.09, 127.84, 131.92, 132.83, 133.22, 133.59, 133.87, 148.06, 164.30, 182.31(CO), 184.82(CO).

Embodiment 7 (2-tert-Butyl-1(3)H-anthra[1,2-d]imidazole-6,11-dione, No. 8)

All steps for manufacturing the yellow compound No. 8 are identical with the steps of Embodiment 3, except that propionaldehyde is substituted by trimethylacetaldehyde (0.46 g, 5 mmol).




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stats Patent Info
Application #
US 20090253707 A1
Publish Date
10/08/2009
Document #
12193564
File Date
08/18/2008
USPTO Class
514250
Other USPTO Classes
5483017, 514394, 514362, 548126, 544343
International Class
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Drug, Bio-affecting And Body Treating Compositions   Designated Organic Active Ingredient Containing (doai)   Heterocyclic Carbon Compounds Containing A Hetero Ring Having Chalcogen (i.e., O,s,se Or Te) Or Nitrogen As The Only Ring Hetero Atoms Doai   Hetero Ring Is Six-membered Consisting Of Two Nitrogens And Four Carbon Atoms (e.g., Pyridazines, Etc.)   1,4-diazine As One Of The Cyclos   At Least Three Rings In The Polycyclo Ring System  

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