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    • 专利摘要:

    公开号:SU963469A3
    申请号:SU802954167
    申请日:1980-07-25
    公开日:1982-09-30
    发明作者:Шенафингер Карл；Бейерле Руди；Нитц Рольф-Эберхард；Марторана Пьеро；Фидлер Фолкер
    申请人:Касселла Аг (Фирма)；
    IPC主号:
    专利说明:

    (5) METHOD FOR GETTING KINDS OF NED SIDNONIMINES OR THEIR SALTS
    t
    The invention relates to a process for the preparation of substituted sydnonimines of the formula
     v 7-Vffi JC (J N - B
    Yu
    where R is hydrogen, or bromine;
    R is hydrogen, a group —NO, —COR or —SO,
    R -
    hydrogen, C-C-alkyl-, which may be substituted with C -C-alkoxy or phenoxy, cyclohexyl, phenyl, unsubstituted or MONO-, di- or trisubstituted with halogen and / or methyl and / or methoxy.
    benzyl, styryl, C-C-alkoxy, phenoxy, pyridyl or alkoxycarbonyl - group 75 (0, with m O, 1 or 2,
    or a group of 7N-SO R;
    R- - phenyl or stoked;
    R is methyl, phenyl, tolyl or dimethylamino, or their salts.
    It is known that with the action of naoL- (N-methyl-M-nitrosoamino) nitriles of nitric acid or hydrogen chloride in the ether, salts of sydnonimines D 3 are obtained.
    The goal is achieved according to the method of obtaining the substituted ones. Sidnonimine formula (I), consisting in the fact that the compound of the General formula
    N-F-dH -dN
    (.O N0. Substituted 3 amino-dinonimines of the general formula (i) are formed with inorganic or organic acids; salts with acids. Such acids. For example, hydrochloric acid, hydrobromic, phosphoric,: sulfuric, oxalic, milky, vinna, acetic acid, salicylic acid, benzoic acid, citric acid, ascarbinic acid, adipic acid or naphthal n disulfonic acid. Salts with acids are often obtained, mainly the hydrochlorides of the compounds of general formula (J.) directly in the synthesis of the latter. Salts with acids can be used to obtain free compounds of general formula (T ) , by a known method, t, e, by dissolving or suspending in water and alkalizing, e.g., sodium hydroxide, followed by isolation of the desired product. Pharmacologically acceptable salts are preferable / Necessary starting compounds of general formula (s) can be obtained by syn-bromide amine nitrile according to Strecker from amine by reacting with formaldehyde and hydrocyanic acid in a suitable solvent, for example in water, the compound of the general formula first being prepared. bNg - dN with which nitrosation is converted into compound (P). The nitrosation is carried out in the usual manner in a suitable solvent, preferably in water, at. Nitrous acid is usually obtained from alkali metal nitrite and hydrochloric acid. It is advisable to jioeecTM aqueous solution of the compound (Vj) with hydrochloric acid to a pH of 1-3 and add alkali metal nitrite in the form of an aqueous solution to the stirred and cooled solution of the compound. A solution of the obtained compound (I) can be cyclized. It is believed to first dissolve the nitroso compound (LJ) in a suitable organic solvent and carry out the appropriate cyclization in the appropriate case. A compound of the general formula O T® Kx (O where m 1 or 2 is obtained by oxidation of compounds of the general I of the formula Or-K-d-B V, / l @ l Kch-C-K-B or their salts with acids. This oxidation is Use hydrogen peroxide in a suitable solvent, such as glacial acetic acid, at room temperature or slightly elevated temperature (approximately 50-60 ° C). Compounds of general formula (J) and their pharmacologically applicable salts with acids have valuable pharmacological properties. their effect on the cardiovascular system, compared with by a known compound, Molsidomin or similarly acting isosbrbid dinitrate, they exhibit a stronger effect on some properties and / or act longer. They lower, for example, blood pressure and pulmonary artery pressure and presystolic pressure in the left ventricle of the heart and such thus contributing to the relief of cardiac activity in the sense of anti-anginal action, does not cause reflex tachycardia. The anti-anginal effect of the proposed compounds is established by the following method. The tests were carried out on crossbred dogs of both sexes that were under pentobarbital anesthesia (30MO / kg intravenously) or under urethanchloralose (3 ml / kg of a mixture of urethane chloralosis intravenously - 20 mg / kg of chloralosis and 250 mg / kg urethane). Artificial respiration of animals is carried out in a breathing apparatus. Two-Mark-Z-Respirator. Maximum yield carbon dioxide content (measured by an infrared absorption instrument, Uras), 5-S vol. During the whole trial, animals under pentobarbital anesthesia receive a continuous infusion of pentobarbital intravenously (Cmg / kg 6) l / h to achieve a constant depth of anesthesia; animals under urethane-chloral anesthesia do not receive prolonged infusion. Infusion is infused into Vena cephalica. After the test animals have been prepared, another wait (about ONE hour for all hemodynamic parameters to set (steady state). Then the tests are started. Systolic and diastolic blood pressures are measured peripherally in the femoral artery n (3) pressure measurement (Statham-D). A catheter (Millar-TK) inserted through the carotid artery into the left ventricle of the heart shows presystolic pressure in the left ventricle and heart rate. Another catheter inserted into the belt vein is measured e, blood pressure in the pulmonary artery. This test method shows, for example, the following compounds in these doses show significant activity: A - hydrochloride 3 (tetrahydro-1, -thiazin-yl-1,1-dioxide) -sidnonimine B - M-cyclohexylcarbonyl-3- (tetrahydro-1, C-Riazin-k-l-, 1-dioxide -sidnonimine; B -v hydrochloride 3 (-methanesulfonyl-piperlsin-1-yl) -sidnonimine; G-N-ethoxycarbonylcarbonyl- 3- (4-methanesulfonyl-piperazin-1-id) -sidnonimine; D - M-benzoyl-3 - (- methanesulfonyl-piperazin-1-yl) -sidnonimine; E - hydrochloride 3 C -Dimethylamino sulfonyl-piperazin-1-yl) -sidnonimine W - (D-chlorobenzoyl) -3- (tetrahydro-1, + - thiazin-4-yl-1, 1-dioxidinenonimine; 3 - hydrochloride C - (thiomorpholino) -sidnonimine;, and - N-propionyl-3- (i-dimethylaminosulfonyl-piperazin-1-yl) -sidnonimine hydrochloride (see table). For therapeutic use, mixing 1t of pharmacologically applicable salts with acids of new compounds or new compounds in free form with conventional pharmaceuticals such as fillers, carriers, plastering agents, swelling, scaling agents, thickeners or thinners, solvents or thinning agents or long-lasting effects that can be administered intraperitoneally and parenterally. As pharmaceutical preparations, tablets, dragees, pills, , capsules, solutions, suspensions or emulsions, and, in addition to new active principles, you can also add to i serving and stabilizing media, emulsifiers, substances with a buffer action, as well as one or more other tera Pheutically active substances. Other therapeutically active substances are, for example, p -receptor blockers, for example propranolol, pindolol, metoprolol; vasodil tori, for example carbochromes; sedatives, such as barbitric acid derivatives, 1, -benzodiazepines and meprobamate; diuretics, such as chlorothiazide; heart tonic agents, such as digitalis preparations; blood pressure reducing agents, for example, hydralazine, dihydralazine, prazonin, clonidine, alkaloids of plants of the genus Rauwolfia, which lower the level of fatty acids in the blood, for example, bezafibrate, fenofibrate, means for preventing thrombosis, for example, fenprocumone. Pharmaceutical preparations generally contain 0.1-50 mg, preferably 0.5-10 mg per dose. The following examples serve to better explain the invention, the data in percent means the weight O, if nothing else is indicated. Example 1. 3-thioformolino-synonimine hydrochloride. 17.7 g of aminothiomorpholine is dissolved in 100 g of water. By adding dropwise concentrated hydrochloric acid, the pH value of k is adjusted in the solution, then cooled to, and a solution of 7, k g of sodium cyanide in water is added dropwise. After the addition of 12 g of formalin 0, the solution is left to stand overnight (pH 7-7.5). After that, with concentrated hydrochloric acid, the pH value of DOV9DYAT to 2, cooled to 0 ° C, and a solution of 10 g of sodium nitrite in 30 g of water is slowly added dropwise to the solution, and the mixture is stirred for one hour and extracted twice with 50 ml of complex ethyl acetate and the organic phase is dried over sodium sulfate. After dilution of this solution, 150 ml of methanol are introduced while cooling with water 15 g of hydrogen chloride and continue to stir for one hour. Then the solid product is sucked off, the mother liquor is concentrated and recrystallized from ethanol, T. pl. 18I-183 C (with decomposition). Output 18.5 g (83% of theorest Analogously to example 1, starting from 4-amino-tetrahydro-1,4-triazine-dixi da, + -amino-tetrahydro-1, 4-triazine oxide, 1-amino-4-methanesulfonyl- piperazine, 1-amino-1-dimethylaminosulfonyl-piperazine, 1-amino-4-I-toluenesulfonyl-piperazine, the following proposed compounds can be synthesized: hydrochloride 3 (tetrahydro-1, -thiazin-yl-1,1-dioxide) -sindoneimine (mp. 20b-208C (with decomposition), yield 85% of theoretical.) 3- (tetrahydro-1, C-thiazin-4-yl-1-oxide) hydrochloride -sidnonimine (MP, 200 201 C (with decomposition), output 80 from theoretical.); Hydrochloride 3 - (- methane e of phonyl piperazin-1-yl) -sindoneimine (mp, pl./degree.), yield 88 from theoretical,); 3- - -toluenesulfonyl) -piperazin-1-yl / syn donimine hydrochloride (1. pl. (s decomposition), output 78 from theoretical.); hydrochloride (dimethylaminosulfonyl) -piperazin-1-yl / -sidnonimine (T. pl, 193-19 C (with decomposition), yield 82% of theoretical,). The 1-amino-methanesulfonyl-piperazine required in the starting material can be synthesized as follows. 10 g of methanesulfonyl-piperazine is dissolved in 50 ml of water, after adding 6.2 ml of concentrated hydrochloric acid, a solution of 5, + g of potassium cyanate in 20 ml of water is added dropwise and stirred for k h at room temperature. The precipitation is sucked off and dried. Yield 11 g, -T. square C. 10 g of the dried sludge and g of sodium hydroxide solution are cooled in 80 ml of water to 0 ° C and 0.052 mol of sodium hydrochlorite preliminarily cooled to 0 ° C is added. Then it is stirred at room temperature until there is no more hypochlorite. The aqueous solution of 1-aminomethanesulfonyl-piperazine thus obtained can be directly used for further interaction. Similarly, it is also possible to prepare other starting products of the piperazine series. Example 2 3- (tetrahydro-1, 4-thiazin-yl-1-oxide) -sidnonimine hydrochloride. 17.5 g of 3-thiomorpholino-sided imine hydrochloride are dissolved in 100 ml of ethyl acetic acid. To this solution is added dropwise a g of an aqueous solution of 30% hydrogen peroxide and stirred for one hour at room temperature. After concentration in vacuo, it is recrystallized from ethanol. T, pl. 200-201 C (with decomposition), yield 15.3 g (86% of theor,). Analogously to example 2, when using a large amount of an excess of 30% hydrogen peroxide and under more severe conditions of the reaction, it is possible to synthesize hydrochloride 3 (- (tetrahydro-1, -thiazin-yl-1,1-dioxide) -sidnonimine. Example 3 N-acetyl-3-thiomorpholino-sidnonmina hydrochloride, 6.0 g of 3-thiomorpholino-sidnimine hydrochloride are suspended in 50 ml of acetic anhydride, 10 ml of anhydrous pyridine are added and stirred overnight. The colorless crystals are sucked off and recrystallized from methanol. , 197 C (with decomposition), yield 82% of theor Analogously to this example, the following proposed compounds can be obtained: N-a.cetyl-3- (tetrahydro-1, -thiazine -yl-1, 1-dioxide) -sidnonimine (t, pl. 212-2 ° C (with decomposition) , yield 79% of theoretical,); N-methoxyacetyl-3 (tetrahydro-1, -thiazine-yl-1, 1-dioxide) -sidnonimine (T, mp, 188-192 C (with decomposition), yield 83% from theoretical,); N-acetyl-3S-Dimethylaminosulfonyl-piperazin-1-yl) -sidnonimine hydrochloride (mp. 185 ° C (with decomposition), yield 80% of theoretical); N-acetyl-3 - (-dimethylaminosulfonyl-piperazin-1-yl) -sidnonimine (T, mp ,, 176-177 C (with decomposition), yield 80% of theorem, free base); M-acetyl-3-C + methanesulfonyl-piperazin-1-yl) sydnonimine hydrochloride (T, PL-, 20 C (with decomposition), yield 86% of theoretical); N-acetyl-3- (-methylsulfonyl-piperazin-1-yl) -sidnonimine (T, mp, 23b C (with decomposition), yield 86% of the theoretical, free base; N-propionyl-3- hydrochloride (imethylaminosulfonyl- piperazin-yl) -sidnonimine (T. mp, 179 C (with decomposition), yield 81% of theoretical,); N-formyl-3- (tetrahydro-1, -thiazine-yl-T, 1-dioxy) - Sidnonimin P.96 (T. pl. (with decomposition), yield 87- from teoreth.) Example: N-Pyvaloyl-3 - (- metal phonyl-piperazin-1 -yl) -sidnonimine. 28.3 g of tansulfonyl hydrochloride -pig {erazin-1-yl) -sidnonimine is dissolved in 200 ml of water, then cooled before and with stirring 28 g sodium bicarbonate are added. After that, 2 g of pivaloyl chloride is added and the solution is stirred overnight. The solid is filtered off with suction and recrystallized from ethanol. T. pl. , yield 25.8 g (73% of teoret.1.) By dissolving in methanol and adding methanolic hydrochloric acid, this compound is transferred to the hydrochloride with a melting point (decomposed). Example 5. N-benzryl-3- ( -methylsulfonyl-piperazin-1-yl) -sidnonimine. 5.6 g of CZ hydrochloride + methanesulfonyl-piperazin-1-yl) -oidone mine and 2.8 g of benzoyl chloride are stirred in 50 ml of anhydrous pyridine for one day at room temperature. perature. A fine crystalline precipitate is sucked off and recrystallized to 225 C (with vAut from methanol. Mp 225 C (with decomposition, yield 6.0 g (85% of warming). Analogously to examples 4 and 5, the following compounds can be obtained: N-ethoxycarbonyl -3 (tetrahydro-1, 4-thiazin-yl-1, 1-dioxide) -sidnonimine (mp. 208-210С (with decomposition), yield 89% of theoretical); N-cyclohexylcarbonyl-3 (tetragons po-1, 4-thiazin- | -yl-1, 1-dioxide) -sidnonimine (mp. 160-163 ° C, yield from tert.); N-ethoxycarbonyl-3 thiomorpholino-sidnonimine (mp. 1b6- 1b8 C, 82% yield of toreore.); N-ethoxycarbonyl-3- (tetrahydro-1 + -thiazin-yl-1-oxide ) -sidnonimine (T. pl., yield 81% of theoretical-) (I-chlorobenzoyl-) 3 (tetrahydro 1, + - thiazine - + - yl-1, 1-dioxide) -sidnonimine (T. pl. 248- 2 9 C (with decomposition), yield 88% of toreore.); N-phenoxycarbonyl-3- (tetrahydro-1, 4-thiazin-A-yl-1,1-dioxide) -sidnonimine (mp 213 -215 С (with decomposition), output 85% of teoret.); N-cinnamoyl-CI DIETylaminosulfonyl-piperazine -yl) -sidnonimine T. pl. 190-192С, yield 77% of the theoretical.) .; 12 N-benzoyl-3- (tetrahydro-1, -thiazin-yl-1, 1-dioxide) -sidnonimine (t, pl. 2 5-247 C (with decomposition), yield 86% of theoretical); N-ethoxycarbonyl-3- / - (i-toluenesulfonyl) -piperzin-1-yl -sidnonimine (t, pl. 190-192 s. Yield 7E% of theoretical); N -cyclohexylcarbonyl-3- (methanesulfonyl-piperazin-1-yl) -sidnonimine (mp. (With decomposition), yield 825 from teoret.); M -phenoxyacetyl-3- ("- (I-toluene | sulfonyl) -piperazin-1-yl / -SIDNONmin (t. Pl. (With decomposition),: yield 88% of theoretical);: M -pivaloyl-3 - (tetrahydro-1, A-thiazin-4-yl-1, 1-dioxide) -sidnonimine (so pl. (with decomposition), the output from teoret.); ,, 88% N - (3, 5 -trimethoxy-benzoyl -3- (tetrahydro-1, -thiazin-it-yl-1, 1-dioxide) -sidnonimine (T.PL., yield 80% of teoreth.); M -toxy-carbonyl-3- C-methanesulfonyl-piperazin-1-yl) -sidnonimine (mp. 19 + C (with decomposition), yield 86% of toretore.); M-ethoxycarbonylcarbonyl-3- (tetrahydro-1, 4-thiazin-4- IL-1, 1-dioxide) -sidnonimine (T. pl., yield 73% of theoretical.); N -neope methylcarbonyl-3- (tetrahydro-1, 4-thiazin-yl-1,1-dioxide) -sidnonimine (mp 168-171 C, 32% yield; from theoretical.); N-ethoxycarbonyl-3 (- dimethylaminosulfonyl-piperazin-1-yl), β-sidnonimine T. pl. N-nicotinoyl-3- (methanesulfonyl-piperazin-1-yl) -sidnonimine (mp 206-207 C, yield 85% of theoretical); N-nicotinoyl-3- (tetrahydro-1, 1-yl-1, 1-dioxide) -sidnonimine (t. Pl. 235 C (with decomposition), yield 86% of theoretical.); (2, "-dichlorobenzoyl) -3- (-dimethylaminosulphonyl-piperazic1 or) sidnonimine (T. mp. C, yield 89% of theoretical.); M ethoxycarbonylcarbonyl-3 - (- methanesulfonyl-piperazin-1-yl) -sidnonimine (mp 182®C (with decomposition), yield 79% of theoretical.); N-benzoyl-3- (4-dimethylsulfonyl piperazin-1-yl) -sidnonimine (T. pl. 205-207 C, yield 82% of theoretical.); , 1396 M-phenylacetyl-3 - / + - (i-toluenesulfonyl) -piperazin-1.-yl-sidnonimine (So pl., Yield 83 from theoretical.); M-butoxyacetyl-3 - (- (I-toluenesyl phonyl) piperazin-1 -yl - / - sidnonimine (So pl. 119-121C, yield 83 of theor.); N (k toluenesulfonyl) -3 Ct-MeTansulfonyl β-piperazin-1-yl) -sidnonimine (T. pl. (with decomposition), yield 89% of theoretical.); (I-toluenesulfonyl) -TM (chetoragide ro-1, "- thiazin-yl-1, 1-dioxide) -sidnonimin (T. pl. 167-169 C, yield 90% of theoretical.). Example 6. N-nitroso-3 (tetrahydro-1, A-thiazin-yl-1, 1-dioxide) -sidnonimine. 5.1 g of hydrochloride 3 (tetrahydro-1, -thiazin-yl-1, 1-dioxide) -sulfonimine are dissolved in 30 ml of water. After cooling, a solution of 1 g of sodium nitrite in 15 ml of water is added dropwise to the mixture, stirred for one hour, then sucked off. T. pl. 128-130С (with decomposition), yield g (78% of the theoretical,). Example 7. I-ethoxycarbonyl-C C-methanesulfonyl-piperazin-1-yl) -bromine-singimine. 3.2 g of N-ethoxycarbonyl-3 (methanesulfonyl-piperizin-1-yl) -mini min are suspended in tO ml of chloromethane. 3.2 g of N bromo-cycinimide are added in small portions and then the mixture is heated for 30 minutes to 50-60 ° C and vigorously stirred; After cooling with ice water, colorless crystals are filtered off with suction and crystallized from methanol. T. pl. 120-122 C (with decomposition), yield 3.0 g (63% of theor.). Analogously to example 7, N-ethoxycarbonyl-3- (tetrahydro-1. -Thiazine-i-yl-1, 1-dioxide) - -bromo-sydnonimine is obtained with m.p. 160-164 ° C (with decomposition), 75% yield from theoretical.
    17 claims
    A process for the preparation of substituted sidechloimine of the general formula (J).
    18
    where A is as defined, cyclized in a solvent and in the presence of a mineral acid with cooling to obtain the salt of a compound of the general formula (111)
    CH I where R is hydrogen or bromine; -. R is hydrogen, -NO group, -COR hydrogen, C - / - C-alkyl, which can be substituted with C-alkoxy or phenoxy, the cycle is hexyl, phenyl, unsubstituted or mono-, di- or trizamylenny halogen and / or Metall and / or methoxy, benzyl, styryl, C.-C-alkoxy, phenoxy, pyridyl or C-C alkoxycarbonyl; A is the group S (0) j, with IT 1 or 2, or the group -; R4 is phenyl or tolyl; R is methyl, phenyl, tolyl or di-methylamino, or their salts, which means that the compound of the general formula (II) / -1 N-N-CH „-CM VJ 1 which is either isolated or nitrosated in the case of the compound (1 ) where the group is -NO, or is acylated with an appropriate acid anhydride or acid halide in the case of the preparation of compounds. , Hl where R is the group —OR or, or reserve with N-bromosuccinimide in a solvent medium with cooling in the case of preparing compounds (I), where R is bromine and / or oxidized with hydrogen peroxide in a solvent medium and in the presence of acetic acid, compound (1) where A is the group S of the compound (I), where A is the group 7S (0) where m is 1 or 2, followed by isolation of the target product in free form or in the form of a salt. Sources of information taken into account in the examination 1. Heterocyclic compounds. Ed. R. Elderfield-. M., Mir, vol.7, 1965, p. 393.
    权利要求:
    Claims (1)
    [1]
    Claim
    The method of obtaining substituted sydnonimines of the General formula
    A N - N --- C - R * where A has the indicated meanings, is subjected to cyclization in a solvent medium and the presence of a mineral acid upon cooling to obtain a salt of a compound of the general formula (III) where R is hydrogen or bromo; 3
    R 4 is hydrogen, a group —NO, —COR OR —SQjJ ^ ·;
    R is hydrogen, C ^ -C 6 -alkyl, which may be substituted by C ^ -C ^ -alkoxy or phenoxy, cyclohexyl, phenyl, unsubstituted or mono-, di- or trisubstituted by halogen and / or methyl scrap and / or methoxy, benzyl, styryl, C * -C ^ alkoxy, phenoxy, pyridyl or C ^ -C ^ alkoxycarbonyl;
    A is a group S SfO) * ^, moreover, it = 0, 25 1 or 2, or a group> N - SO ^ R;
    r4 is phenyl or tolyl;
    R * is methyl, phenyl, tolyl or dizo methylamino group, or their salts, which consists in the fact that the compound of General formula (H)
    R ~ 3
    And N - N - CH, - CN! 2
    N0
    And N __ f
    NH which is either isolated or nitrosated in the case of obtaining the compound (1) where R l is the group —NO, or acylated with the corresponding acid anhydride or galoid anhydride in the case of the preparation of compounds *,.
    where I * 2 are groups — COR ^ or —SO ^ R 9 ·, or brominated with N-bromosuccinimide in a solvent medium upon cooling in the case of obtaining compounds (|.), where R 1 - bromine and / or oxidized with hydrogen peroxide in a solvent medium and in the presence of acetic acid of compound (1), where A is a group 7 S of compound (1), where A is a ZSiO group) * ^, where m = 1 or 2, followed by isolation of the target product in free form or in the form of a salt .
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    引用文献:
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    DE1695897C3|1966-07-04|1979-02-15|Takeda Chemical Industries Ltd|N-acyl-sydnonimines, their salts, processes for their preparation and medicaments containing these compounds|
    DE1670127A1|1966-08-09|1970-12-03|Boehringer Sohn Ingelheim|Process for the preparation of new substituted 3-amino-sydnonimines|
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    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    DE19792930736|DE2930736A1|1979-07-28|1979-07-28|PHARMACOLOGICALLY ACTIVE, SUBSTITUTED 3-AMINO-SYDNONIMINE, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE|
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