前苏联专利SU1447277A3 Method of producing polycyclic aromatic derivatives of alkanol or salts thereof

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专利摘要:
Compounds of the formula (I) or monomethyl or monoethyl ethers thereof, the compounds including their ethers containing no more than 28 carbon atoms in total, or esters or salts thereof; wherein Ar is selected from the group comprising: optionally substituted by one or two substituents which taken together contain not more than four carbon atoms in total and which are the same or different and are selected from halo; cyano; Ci-3 alkyl or Ci-3 alkoxy each optionally substituted by hydroxy or C1-2 alkoxy; halo substituted C1-2 alkyl or C1-2 alkoxy; a group S(O)nR5 wherein n is an integer 0,1 or 2 and R5 is C1-2 alkyl optionally substituted by hydroxy or C1-2 alkoxy; or Ar is optionally substituted by a group NR6R7 containing not more than 5 carbon atoms wherein R6 and R7 are the same or different and each is a C1-3 alkyl group or NR6R7 forms a five or six membered heterocyclic ring optionally containing one or two additional hetero atoms; R' is Ci-3 alkyl substituted by hydroxy; R2 is hydrogen, C1-3 alkyl or hydroxymethyl; R3 and R4 are the same or different and each is hydrogen, methyl or ethyl; R1, R2, R3 and R4 taken together containing not more than five carbon atoms; or the group: wherein -C-C- is a five or six membered saturated carbocyclic ring containing two or three hydroxy groups; Ra is hydrogen, methyl or hydroxymethyl; R9 and R10 are the same or different and each is hydrogen or methyl; R11 is hydrogen, hydroxy, methyl or hydroxymethyl; R5, R9, R10, R11 and the -C-C- ring taken together containing less than seven carbon atoms which have biocidal, and particularly antitumour, activity are described as are methods for their preparation, their use in medicine and pharmaceutical formulations containing them.
公开号:SU1447277A3
申请号:SU853982431
申请日:1985-12-02
公开日:1988-12-23
发明作者:Вальтер Бейр Кеннет
申请人:Дзе Велкам Фаундейшн Лимитед (Фирма)；
IPC主号:

专利说明:

CM
The invention relates to a method for the preparation of new biologically active chemical compounds, specifically to a method for producing polycyclic aromatic derivatives of alkanol or their salts having biocidal activity, which suggests the possibility of using these compounds in medicine as anti-tumor compounds.
The purpose of the invention is to obtain new polycyclic aromatic alkanol derivatives, showing a new kind of activity for this p - yes compounds.
All solvents used are of the necessary grade and are used without further purification, but with subsequent aids, additional treatments. The tetrahydrofuran is dried by distillation over an alloy of Na / K in a nitrogen atmosphere and then immediately used. Toluene is distilled over CaH under nitrogen and stored over a 3A molecular sieve. The chemicals used are of the required grade and are used without further purification, unless otherwise specified.
Preparative liquid chromatography at high pressure was carried out using a Waters Prep LC / System 500 A device using two columns filled with each 500 g of silica gel (SiO-2). The inserts of SiO, j used for cleaning are inserts made of C 11 glyage for pulsed chrome. Photographs (E. Merck, silica gel 60, sieve N 230-400, i.e. 0.0620, 037 mm). A funnel filled with sintered glass and having a matching wrap is filled with about 3/4 SiO / j, and a tap is put on the bottom of the funnel. A piece of filter paper is then placed on top of the SiO and a solution of the material being cleaned is introduced onto this top part. Due to careful sucking through the filter, a portion of the eluting solvent is moved through the silica gel insert. Fractions of an appropriate volume are combined as necessary and further processed. Satisfactory elemental analysis data are obtained for all of the compounds listed below as examples.
Example 1. A. Chrysene-6-carboxylic acid.
Chrysene-6-carbaldehyde (10.0 g, 39 mmol) and ice acetic acid (1000 ml) are introduced into a round-bottomed flask equipped with a condenser, a bubbler to pass through nitrogen and a magnetic stirrer. The reaction mixture is heated to 50 ° C. A solution of VG2 (6.2 g, 39 mmol, 2.0 ml) in 10 ml of glacial acetic acid is added dropwise to the resulting solution. The reaction mixture is heated to 80 s for one hour, treated with HjO (1 mp) and cooled. The resulting solid is filtered and washed with water. The solid is recrystallized twice from a mixture of tetrahydrofuran-toluene in a ratio of 1: 1, then twice from tetrahydrofuran, and as a result, after drying, 3.3 g of chrysene-6-carboxylic acid with mp. 305 ° C.
In chryseloyl chloride.
Chrysene-6-carboxylic acid (2A, 3.3 g, 13 mmol) and SOCl (syrup, 100 ml) are introduced into a round-bottomed flask equipped with a condenser, a bubbler for passing through nitrogen and magnetic mesh. After slow heating, the reaction mixture is heated under reflux with a phlegm formation for two hours, cooled and excess SOCl is removed. The crude solid is suspended twice in toluene (200 ml) and the solvent is removed in a rotary evaporator. This crude oil (3.5 g) is then used without further purification.
Co N-C2- (1,3-Dioxy-2-methyl) propyl} -chrizene carboxamide.
In a round-bottom flask equipped with a condenser, a bubbler to pass nitrogen, and a magnetic stirrer, 6-chrysene chloride (3.50 g, 12 mmol), 2-amino-2-methyl-1,3-propanediol (2.53 g , 24 mmol) and dehydrated tetrahydrofuran (200 ml) „The mixture is heated under reflux for four hours. A white solid is formed during this time. The reaction mixture was poured into water (500 ml) and filtered. The solid is dissolved in ethyl acetate (700 ml),
31А47277
washed with water (3 x 500 ml), saturated with a NaCl solution (2 x 500 ml), dried () and concentrated, giving 4.12 g of a crude white solid. This solid is dissolved in ethyl acetate (500 ml), filtered through a sintered glass funnel and concentrated to a volume of 200 ml. The hot solution is diluted to 400 ml with hexane. The crystals formed are filtered and again recrystallized from a mixture of ethyl acetate /
I p n m e p 2. 2- (6-Chrysenylmethyl) amine -2-methyl-1,3-propanediol is treated with gaseous HC1 in zta-nol to give (+ -) - (2R, 3R) -2- (6-chrysenyl) methyl amino-2-methyl-1,3-butanediol hydrochloride with m.p. 236.0- 237.5 s (decomposed), CHjOH / Et O.
PRI me R 3. 2- (6-Chrysenyl-1Q tyl) amino -2-methyl-1,3-prop-odiol-lactate
A mixture of 2- (6-chrynylmetsh1) amino - 2-methyl-1,3-propane diol (3.45 g, 10 mmol) and 85% lactic acid
filtered and dried in va-it (1.04 g, 10 mmol) in methanol (500 ml)
hexane
Kum furnace, resulting in 2.06 g (47.8%) of H-C2- (1,3-dioxy-2- -methyl) propyl J-chrysenecarboxamide with so pl. 170-171 ° C.
D. 2-С (6-Хр.изекиилметш1) amino 2-methyl-1,3-propanediol-methanesulfonate.
Into a round bottom flask equipped with a condenser, a bubbler to sell until refluxed and filtered through a fritted glass funnel. The solvent is removed using a rotary non-2Q par, resulting in a more solid material. It is crystallized (a mixture of CHjOH / Et O) three times, resulting in a yield of 1.84 g (42.2 lactate-C (6-chrysenylmethyl)
start up nitrogen and a magnetic stirrer, 25 amine -2-methyl-1,3-propane diol, so pl.
1b3-1b4 co
Example 4., 2 (6-Chrysensch-1methyl) amino -2-methyl-1,3-propanediol citrate.
(1,3-Dioxy-2-methyl) propyl-chrysenecarboxamide (1.0 g, 2.8 mmol) and dehydrated tetrahydrofuran (100 ml) were added. A mixture of 2- (6-chrysenstmethyl) amino-Li Li A1H4 (0.53 g, 14 mmol) in the form of 30 2-methyl-1,3-propa1iol (3.45 g
several servings. The reaction mixture darkens rapidly to obtain a thick brown color with gas separation. The reaction mixture is stirred in (10 mmol) and citric acid (1.92 g, 100 mmol) in methanol (500 ml) is heated until it dissolves, then the mixture is filtered four times a day. 2- (6 -Chrysylmethyl) amine -2-methyl-1,3-propanediol is treated with gaseous HC1 in ztaol to give (+ -) - (2R, 3R) -2- (6-chrynyl) methyl amino-2-methyl- 1,3-butanediol hydrochloride with m.p. 236.0- 237.5 s (decomposed), CHjOH / Et O.
PRI me R 3. 2- (6-Chrysenylmethyl) amino -2-methyl-1,3-propane oiol lactato
A mixture of 2- (6-chrynylmetsh1) amino - 2-methyl-1,3-propane diol (3.45 g, 10 mmol) and 85% lactic acid
(1.04 g, 10 mmol) in methanol (500 ml)
DEFINED until refluxed and filtered through a sintered glass funnel. The solvent is removed using a rotary non-evaporator, resulting in a more solid material. It is crystallized (a mixture of CHjOH / Et O) three times, resulting in a yield of 1.84 g (42.2 lactate-C (6-chrysenylmethyl)
A mixture of 2- (6-chryseenshtmethyl) aminoJ2-methyl-1, 3-propa1 schiol (3.45 g
10 mmol) and citric acid (1.92 g, 100 mmol) in methanol (500 ml) is heated until it dissolves, then the mixture is filtered
night at room temperature, 35 P funnel with a porous glass
then refluxing with refluxing for 14 hours. The reaction mixture is quenched by the addition of saturated
plate Next, the solvent is removed, resulting in a crude product — a white solid. His bring to a boil
solution of Na.jS04. (10 ml), and then water 40 absolute ethanol (2x300 mp) (50 ml). This reaction mixture is extracted with ethyl acetate (3x200 ml). The ethyl acetate layers are combined, washed with water (200 ml), saturated NaCl (3 X 200 ml), dried (over
and filtered, resulting in a white solid. It is then subjected to recrystallization twice (a mixture of CHjOH / Et O), filtered, 45 dried overnight in a vacuum oven, resulting in a yield of 1.24 g of citrate 2-C (6-x-phenylmethyl) amino-2-methyl-1,3 - propanediola, m.p. 146-151 C. Methods are used to evaluate the antitumor activity of new alkanol derivatives. Which are listed for tumors in a therapeutic research development program (Cancer Treatment Department, National Cancer Institute).
), filtered and concentrated to give a tan solid, 2- (6-chrysis-methyl) amino, 3-2-methyl-1,3-propanediol, m.p. 200-202 ° C. This solid is dissolved in absolute ethyl alcohol EtOH (25 ml) and in. C. 808 H (0.5 ml), heated and filtered. The solid is diluted with hexa - nome to a volume of 500 ml, filtered and recrystallized to give 0.21 g (16.9%) of the title compound, m.p. .227-228 ° C.
absolute ethanol (2x300 mp)
and filtered, resulting in a white solid. It is then recrystallized twice (CHjOH / Et O mixture), filtered, dried overnight in a vacuum.
chi, resulting in a yield of 1.24 g of citrate 2-C (6-chloromethyl) amine-2-methyl-1,3-propanediol, m.p. 146-151 C. Methods are used to evaluate the antitumor activity of new alkanol derivatives. Which are listed for tumors in a therapeutic research development program (Cancer Treatment Department, National Cancer Institute).
Test against Lymphocytic Leukemia P388 / 0.
In this test, use CD2-F of the same sex, weight
which was 20 + -3 g. 10 live P388 / 0 tumor cells were administered intraperm o day using control and test animals. In each trial, several dose levels are used to estimate also the LDjo value for each compound, the group for each dose consists of six animals. Test compounds are prepared either in physiological saline solution containing 0.05% Tween 80 compound or in distilled water containing 5% dextrose, and administered to the animals by intraperitoneal route on days 1, 5 and 9 of tumor implantation. Doses are determined in mg / kg, depending on the body weight of each animal. The day of death for each animal is recorded, the average value for each group is determined, and the ratio of the average lifetime dp to the treated (T) versus control (s) group is calculated. The criterion of activity is the value of T / C to X 100 120%.
With an optimal dosage of 45 - 600 mg / kg T / C X 100% (excluding those who survived on the 20th day) is (+130) - (+ 300),
Lymphoid leukemia L 1210, Procedure; This test is identical for P 388/0 then
except that the number of cells is L 1210, “of the soft tissue, then cut
. f f% .. t
implanted on day U, is Yun. In the test, strains were used, and cubes of 2-3 mm in size were used as the activity criteria. Each bic is implanted by the subcutaneous route into the abdominal thoracic area under sterile conditions on day 0. Each
the rank of the TS-X 100 125%. At optimal 40, several doses are applied with
Noah dosage .110 - 150 mg / kg T / C x
X 100%, excluding survivors
on day 30, it is (+194) (+252).
Melanotic B16 Melanoma.
In this test, B6CO3-E mice of the same are used. sex, having a weight of 20 + 3 g. A suspension of B16 cells is prepared from a necrotic part of hard tumor tissue obtained from a donor mouse. One gram of the tumor is homogenized in 9 ml of ice-cooled brine and filtered through a 100 mesh sieve.
so as to estimate the LD 2 o dL value of each compound. In the group, ten animals are used for each dose, and in the untreated control group, Zyhivotnk. Test compounds are prepared either in physiological saline solution containing 0.05% Tween 80 compound, or in distilled water containing
50 5% dextrose, and then they are administered intraperitoneally by the method on days 1, 5 and 9 after tumor implantation. Doses are determined on a mg / kg basis according to the weight of each animal.
(O, 149 mm) from c (for removal of residues 55, the 20th day of the animals is approved at
tissue. O, 5 P1 of the resulting Vernier measuring fork is measured
those fluids are injected intraperitoneally with the largest (L) and smallest sizes
method every animal. The dosage (W) of each tumor. The weight of the tumor is determined in the same way as in the test of formula L (W) 2/2 Cree.
P388 / 0 and L 1210. Fix the day of death of the animal for 60 days, and then calculate the T / C ratio, as in tests P388 / 0 and L 1210. At an optimal dosage of 30-100 mg / kg T / Cx. X 100%, excluding those remaining on the 30th day, is (+143) - (+ 200).
Test against Sarcoma M5076.
This type of sarcoma has the form of a solid tumor, which appears in mice of the C57B1 / 6 strain in the ovaries, and is further processed into ascites form for intraperitoneal use. The procedure of this test is identical to that used for P388 / 0, using the strain WbSZ-Fj, and the T / C x 100/125% value serves as a criterion of activity. At an optimal dosage of 85–105 mg / kg T / C X 100%, excluding the survivors on day 30, it is (+ 1b2) - (+ 168).
Test against Cancer 1Solon
Zy
This tumor is caused in mice strain C57B1 / 6 by chemical means, and then maintained in the form of a solid 30 opgholi. The grown solid tumor is then cut out under aseptic conditions in a donor mouse and placed in sterile saline. The tumor is expected to come from necrotic and conjugate. f f% .. t
on cubes of 2-3 mm in size. Each bic implanted subcutaneously into the abdominal thoracic region under sterile conditions on day 0. Each
40 trials apply several doses with
so as to estimate the LD 2 o dL value of each compound. In the group, ten animals are used for each dose, and in the untreated control group, Zyhivotnk. Test compounds are prepared either in physiological saline solution containing 0.05% Tween 80 compound or in distilled water containing
50 5% dextrose, and then they are administered intraperitoneally by the method on days 1, 5 and 9 after tumor implantation. Doses are determined on a mg / kg basis according to the weight of each animal.
The activity limit is T / C X 100 42%.
With an optimal dosage of 65-150 kg / kg T / C X 100%, it is 23-38.
Test against Lewis Lung Cancer.
This tumor arises spontaneously in the lungs of C57B1 / 6 mice and is supported by transplantation under the skin in this strain. A solid tumor is obtained under aseptic conditions.
and placed in sterile saline plant- (Stanton's Medium or a Modified Thief. Pieces of Natural Tumor Tone-15 Diamond's Medium).
they are crushed with scissors. Evaluation of the test: O - inhibit through the stainless steel sieve is not observed; (-1) - inhibiting steel of 200 mesh (0.074 mm), with a rate of 1-25%; (-2) - inhibiting suspension of 10 living cells from intracellular cells from tissue cells
20
bating is 26-50%; (-3) - inhibition is 51-75%; (-4) - inhibition is 76-100%.
into the tail vein of BD-F. mice of the same sex weighing 20 ± 2 g. In each trial, several doses are used in order to estimate the value for each compound. The group for each dose includes ten animals and 20 animals in the untreated control group. The test compounds were prepared and applied according to the procedure for P388 / 0. A day of death was recorded for each animal, the average value for each group was determined, and the ratio of the average lifetime for the treated (T) to control (C) group was calculated. The criterion of activity is the value of T / C x 100-7 / 140%. With an optimum dosage of 85–105 mg / kg T / C X 1.00% is (+191) - (+ 222).
Tests against Candida albicans
The antifungal test against Candida albicans (CN 1863) was carried out with slight modifications using a combination of assays with dilution of broth and agar. The MIC is 30-100 mg / L.
Antibacterial test.
The antimicrobial test against Mycoplasma smegtnatis (S3264) and Streptococcus pyogenes (CN 10) ocjr-s was performed with slight changes using standard assays related to the dilution of the agar. MIC 10 mg / lo
Test against Mycoplasmer Smegmatiso
Antibacterial test result against Mycoplasma Smegmatis

78
(53264): MIC is from 5 to 10 mg / L.
The test against protozoa Frichomonas vaginalis was carried out using the methods described by R. M. Michael.
Results of activity against protozoa Frichomonas vaginalis (in laboratory conditions)
Dose, mg / l Result 40-4
40-4
Evaluation Test: O — No inhibition noted; (-1) - inhibition is 1-25%; (-2) - ingi-
0
five
35
bating is 26-50%; (-3) - inhibition is 51-75%; (-4) - inhibition is 76-100%.
Use against Nippostrongylus brasiliensis.
Activity against Nippostrongylus brasiliensis worms is analyzed using the methods described by D.J. Jenkins et al.
Results of activity against the weed Nippostrongylus brasiliensis (mature stages of development): MIC is 7/50 mg / l o
Test against Eimeria tenella.
Activity against the simplest Eimeria tenella is analyzed using the methods described by V.S. Latter and D.UnlsonoMo.
Test results against the simplest Eimeria tenella under laboratory Q conditions:
Dose, mg / l Result 0.31-4
1.25-4
Test evaluation: O - no inhibition; (-1) - inhibition is 25%; (-2) - inhibition is 26-50%; (-3), - inhibition is 51 - 75%; (-4) - inhibition is 76-100%
LD JP for these compounds (one dose; -OD - 1 male baby) is 85-250 mg / kg.

权利要求:
Claims (1)
[1]
g Formula of invention
The method of obtaining polycyclic aromatic alkanol derivatives of the general formula
0
- h
ten
Their salts are also distinguished by the fact that a compound of the general form
c: n21 ns-B2
CH2-OH
R, - C, -Cj R, -C, -C, j
alkyl substituted
hydroxy;
alkyl, provided
that K, and Rj, are taken
contain not together
more than five atoms
carbon,
Redditor I.Shulla
Tehred M. Khodanich Proofreader E. Lonchakova
Order 6756/58
Circulation 370
VNIIPI USSR State Committee
for inventions and discoveries 113035, Moscow, Zh-35, Raushsk nab., d, 4/5
I G CO NH-C-R2
ten
CH2-OH
where R, and R2 have the indicated values
neither
subjected to reduction with a metal hydride in an inert solvent, and the desired product is prepared in free space or salt.
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法律状态:

优先权:

申请号 | 申请日 | 专利标题

GB838313571A|GB8313571D0|1983-05-17|1983-05-17|Chemical compounds|

APAP/P/1984/000003A|AP1A|1983-05-17|1984-07-16|Polycyclic aromatic compounds|

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