• 专利附录
  • 专利说明
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    • 专利摘要:

    公开号:SU1001856A3
    申请号:SU813241898
    申请日:1981-02-12
    公开日:1983-02-28
    发明作者:К.Тиме Петер；Франке Альбрехт；Ленке Дитер；Дитер Леманн Ханс；Грис Иозеф
    申请人:Басф Аг (Фирма)；
    IPC主号:
    专利说明:

    Acid addition salts are generally prepared by mixing the free base or its solution with an appropriate acid or its solutions in an organic solvent, for example, a lower alcohol such as methanol, ethanol or propanol or a lower ketone, such as acetone, methyl ethyl ketone or methyl isobutyl ketone, or ether, such as diethyl ether, tetrahydrofuran or dioxane. To better isolate the crystals, mixtures of the mentioned solvents can also be used. In addition, we can obtain pharmaceutically compatible aqueous solutions of acid addition compounds of phenylpiperazihyl derivatives of general formula (1) by dissolving the free base of general formula (1) in aqueous acidic growth, The proposed compounds and their physiologically compatible acid addition salts are suitable as drugs with a blood pressure lowering effect for treating hypertension. Blood pressure lowering effects are tested on rats. Urapidil, 1 56 the hypotensive agent urapidil (0 (2-methoxyphenyl) -1-piperazineyl propyl -1, 3 dimethyluracil) is used as a substance for comparison: males of rape; Sprague-JDawley strain weighing 220-280 g under urethane anesthesia (1.78 g / kg intravenously) G Blood pressure is measured in blood in the carotid artery. The substance is administered intravenously into the vein of the vein. As a ED, 20% examine doses (mg / kg) which contribute to a 20% decrease in blood pressure. In addition to lowering blood pressure, studies acute toxicity (LD 50, mg / kg) in the to-to groups is possible (ec NMRI mice weighing 22-27 g when administered intraperitoneally. Therapeutic breadth is the quotient of dividing LD 50 by ED 20%. The proposed compounds have a strong lowering blood pressure action (see table). It follows from the table that the effect of the proposed compounds is 2.5–22.5 times higher than the effect of the comparative substance urapidil. Those: the width of the drug is 13 times greater than
    NOTE: 1. On rats, urethane anesthesia, administration: intraperitoneally. 2. Relative action, Urapidil 1,00, 3. Mouse, introduction: intraperitoneally. LD go, ED 20%
    HoBble compounds can be used in the form of conventional galenical preparations in solid or liquid form, for example, in the form of tablets, capsules, powder, granules, dragees, or solutions. They can be obtained in a known manner. Thus the active ingredients can be processed with suitable pharmaceutical auxiliaries, such as talc, gum arabic, sucrose, lactose, starch, cereal or corn starch, magnesium stearate, alginates, tragacanth, carrageenate, polyvinyl alcohol, polyvinylpyrrolidone, aqueous or nonaqueous carriers, wetting mi, dispersants, emulsifiers and / or preservatives. The preparations obtained in this way contain the active principle usually in an amount of 0.001-99-weight.
    Preferred formulations are preparations suitable for oral administration. These kinds of drugs are, for example; tablets, film tablets, pills, capsules, PILULES, powders, solutions, suspensions or preparations with a delayed release of the active principle for a long period of time. Parenteral formulations such as injectable solutions are also used. Further, the following should be mentioned as formulations and suppositories. Suitable tablets can be prepared, for example, by mixing the active principle with known adjuvants, for example inert diluents, such as glucose, sugar sorbitol mannitol, polyvinylpyrrolidone, calcium carbonate, calcium phosphate or milk sugar, by means of swelling, for example, corn starch or alginic acid, binding agents, t such as starch or gelatin, substances that impart lubricity, such as magnesium stearate or talc, and / or agents to achieve the described inhibition of the preparation, such as carboxypolymethylene, carboxymethylcellulose, acetate phthalate or polyvinyl acetate. Tablets may also consist of several layers. Accordingly, pills can be obtained by coating the obtained tablets similarly used for coating pills with means such as collidone or shellac, gum arabic, talc, titanium oxide, sugar. In this case, the dragee shell may consist of several layers, and
    but use the excipients mentioned above in connection with the tablets.
    Solutions or suspensions with active principles can additionally:
    contain flavoring agents such as vanillin or orange extract. In addition, they may contain suspending agents containing carboxymethylcellulose
    sodium, or preservatives, for example p-hydroxybenzoates. Capsules containing active principles can be obtained, for example, by mixing the latter with an inert carrier, such
    like milk sugar or sorbitol, and in gelatin capsules. Suitable suppositories can be prepared, for example, by mixing with the carriers envisioned for this. For example, neutral fats or polyethylene glycol, or their derivatives. The formulation of the proposed compounds depends on the age, condition and weight of the patient, as well as the type of preparation. Typically, the daily dose of active principle is 5-100, preferably 10-80 mg. Getting the original compounds. Example 1. Ortho-1, 3,4-oxadiazolyl-2-phenol. 90 g (0.6 mol) of salicylic acid hydrazide and 355.2 g (2 mol) of ortartic acid ethyl ester are heated for 22 hours at reflux temperature. Excess ortoformic acid ethyl ester is distilled off and the solid residue is recrystallized from ethanol. 62.9 g of a colorless crystal are obtained (6.7% of theory); m.p. 112-113PC. PRI me R | 1. Ortho- (5-methyl-1, 3, -oxadiazolyl-2 -) - phenol. 90 g (0.6 mol) of salicylic acid hydrazide and 388.8 g (2 mol) of orthoacetic acid triethyl ester are heated in 500 ml of n-propanol for 8 hours at reflux temperature. After cooling, the precipitate is filtered off with suction and recrystallized from toluene (petroleum ether). 47 g of colorless crystals are emitted (26.7 from the theory) so pl. 7 + -7b S.: 91 Example IG. Meta-1, 3, -Oxadiazolyl-2-phenol is obtained as in Example 1. 83 g of colorless crystals are obtained (86% of theory)} m.p. 215 216C. , E and IV. Meta- (5-methyl-1, 3, toxadiazolyl-2) -phenol was prepared as in Example II. Get 9+ g of colorless crystals (8E% of theory), so pl. 174-17b with. An example. Pair-1.3. -oxadia-zolyl-2-phenol is obtained similarly to Example 1. 87 g of colorless crystals are obtained (89.5% of theory) t, pl. 215 ° C Example. The pair - (5-methyl-1, 3,4-oxadiazolyl-2) -phenol is obtained in the same way as Example I, 101 g of colorless crystals are obtained (9b% of theory t „pl„ 232 ° C. Pr and a er Um 2,3 Epoxypropy si-2- (1,3, -oxadiazolyl-2) -benzolo Analogously to the example, Y III has half of it, 3 (55% of theory) light yellow oil, which shows the expected NMR spectrum: H-NMR ( SOSTS):, 5 (1 H, oxadiazole-proton); (D 7,, 0 (k Hyjb aromatic protons); k, 2 (1 lU,, 4 (GN)) ((2 Hd) for epoxypropyl protono Example Y111. 2 , 3 Epoxypropano si-2- (5 methyl-1, 3, 4-oxadiazolyl-2) -benzene. 1.6 g of sodium hydride are used as a suspension in paraffin m after (0.03 mol) in 70 ml of anhydrous tetrahydrofuran and 6.3 g (0.036 mol) of ortho- (5-methyl-1, 3, -oxadiazolyl-2) phenol dissolved in 50 ml of tetrahydrofuran are added dropwise. Then 5 g (0.03 mol) of epibromohydrin was added dropwise, 10 ml of hexamethylphosphoric acid triamide was added to the reaction mixture and stirred for 32 hours at room temperature. The reaction mixture was poured onto 500 ml of an aqueous solution of sodium chloride and shaken with diethyl several times. by ether. The combined ether extracts are dried with anhydrous sodium sulphate and concentrated on a rotary evaporator to a yellow oil. Toluene / hexane gives 5.5 g (66% of theory) of colorless tall crystals; m.p. . Calculated,%: C b2.1, H 5.2, N12, QtaH, (232) Found,%: C 61.6 H 5.3, N .12.1 Example IX. 2,3-Epoxypropoxy-3 (1,3, + -oxadiazolyl-2) -benzene. 56 10. Analogously to Example III, “2 g (53% of theory) of colorless crystals is obtained, Topl. 80-82 0. PRI me R X. 2,3-Epoxypropoxy-3 (5-methyl-1,3, -oxadiazolyl-2) -benzene. Analogously to Example III, 5.7 g (68% of theory) of colorless crystals are obtained; tPLo Example XI. 2,3-Epoxypropoxy- - (1,3, 4-oxadiazolyl-2) -benzene. Analogously to Example III, k g (b9% of theory) of colorless crystals is obtained, mp. 81-82C. Calculated,%: C 60.6; H t, 6, Nl2.8 (218) Found,%: C 61.2, H 5.2, N 12, PRI me R XII. 2,3 Epoxypropoxy Ij (5-methyl-1,3, -oxadiazolyl-2) -benzene / Analogously to the example. In III, 5.9 g (71% of theory) of colorless crystals are obtained; m.p. b5-b7 C. Obtaining the proposed compounds. Example 1. (1, 3, -Oxadiazolyl-2) -foxy-3-C (2-methoxyphenyl) piperazinyl-1-propanol-2. 7.3 g (0.033 mol) of 2,3-epoxypropoi-2 (1,3, -oxadiazolyl-2) -benzene from the example of UPI 6-, g (O., 033 mol) 2-methoxyphenylpiperazine is heated in 50 ml of ethanol 17 h at reflux temperature. The solvent is distilled off on a rotary evaporator, and the oily residue is dissolved in methylene chloride. The solution is washed three times with 50 ml of water, dried with sodium sulfate, filtered and concentrated. 12.6 g (93% of theory) of a light yellow oil are obtained. From ethanol / diethyl ether, the hydrochloride (hygroscopic) is precipitated with hydrochloric acid ethereal, washed with isopropanol and dried under vacuum. Receive, 9 g (29%) of colorless crystals, so pl. 129. Calculated,%: C 5i, 7t H 6 J C1 10.9 N 11.6; About 16.6 Sc. Ld041,5 (if82-). Found,%: C 5.8j H 6.7; STR, 0; N 11.8; O 16.5. EXAMPLE 2. 1-C2- (5-Methyl-1,3, Y-oxadiazolyl-2) -phenoxy-cC2-methoxyphenyl) -piperazinyl-1D-propanol-2 was prepared analogously to example 1 Obtain 3.1 g (20% of theory) of colorless crystals, t, pl. 2kB-2k3 ° C. Calculated,%: C 59.9 N 6.31 SG /, N 12.2; About 13.9 (1) Found,%. C, 59.0; H 6.2, C1 1.1 N 12.1, O, 7 Primer. 1-C2- (1,3, -Oxadium azolyl-2) -phenoxy-jj-G (α-methoxy phenyl) piperazinyl-1-propanol-2, 8.1 g (0.037 mol) epoxypropoxy -2 (1, 3, -oo.xadiazolyl-2) -benzene from Example VII was heated to a s., 7.1 g (0.037 mp) of 3-methoxyphenylpiperazinyl in 100 MP of isobutanol for 18 h at reflux temperature. Processing is carried out analogously to Example K. 11.1 f (62 from theory) of colorless crystals, m.p. 126-128 C. Calculated,% C 5.7; H 5.8, I, 7; N 11.6 2 HC1 1%, C: 5, + | H 6.27 CI 12, N11.9. EXAMPLE 4 (5-Methyl-1, 3-, 4-oxadiazolyl-2) FeiOxyZ-3- {. -13-metoxyphenyl) piperazinyl-1} -propanol-2 is prepared analogously to Example K. 11.6 g (66% of theory) of colorless crystals are obtained in mp 168-20.C. Calculated,% C 51.8 H 6, four; N10, НС 1-2 Н, 0 (533) Found,%. C, 52.6; H 6.4} N 10.6 EXAMPLE 5. 1-C2- (5-Methyl-1,3, 4-oxadiazolyl-2) -phenoxy} - 3- 4- (3-chlorophenyl) - piperazinyl-13-propanol is obtained analogously to example 3. 6.6 are obtained. g (0% of theory) colorless crystals / TbPL. 115-117 C. Calculated,%: C 52.7 H 5, N11, .Oy 2 HC1 (501) Found, I: C 52, i, - H 5.5, N 11.1 P m and me 6 „1- 2-C5-Methyl-1,3, 4-oxadiazolyl-2) -fenesixi-3-C4 (fluorophenyl) piperazinyl-13-prPpanol is prepared as in example 1 in isopropanol as a solvent. 6.6 g (k}% of theory) of colorless crystals are obtained, mp 212-21. Calculated% C 5 ,, And 5,, N11, C1 U, 6 () Found,% t 5.1, H 5.8; N 11.4 C1 14.3 P and m 6 p 7. 1-GZ- (1,3,4-Occdiazolyl2) -foxy-3-3-t4- (2-methoxyphenyl) piperazinyl-13-propanol-2 receive as in example 1 in ethanol as a solvent. Get 3.6 g (22 from theory) of colorless crystals, t, pl. 208-2YU p. 1 56 Calculated, I: C 53.7 N 6.2} N11, t ULOF NS1I, 5 (92) Found,%: C 53.2; H 6.5, N11.0 Example 8, 1-D- (1,3, -Oxca-diazolyl-2) -phenoxy-3-C (3-methoxyphenyl-piperazinyl-1-propanol-2) was prepared as in example 1 in isopropanol as a solvent. 6.6 g (0 from theory) of colorless crystals are obtained, mp, 208-209 C. Calculated, I: C 53.7; H 6.2 N11, qi i6 %% b5HC14.5 H2.0 (it92 ) Found,%: C 53.4, - H 6.4, N11.3 M .... Ouzh r - 1 t II I. s11 Example 9 1-W3- (1, 3, 4-Oxa-. Diazolyl-2) -phenoxy-3 114- (2-ethoxyphenyl) -piperazinyl-1Z-propanol-2 was prepared as in example 1 in isopropanol as solvent. 13.4 g (79% of theory) of colorless crystals t, pl, .211-212 C. Calculated,%: C 55, 4; H 6.0; N11.3 () Found: C 54.7; H 6.3; N 11.0; I will try it. 1-p- (5-Methyl-1,3, 4-oxadiazolyl-2 3-C4- (2methoxyphenyl) -piperazinyl-1H-propanol-2) -phenoxy-3-C4- (2methoxyphenyl) -piperazinyl-1H-propanol-2 is obtained analogously to Example 1. Solvent is obtained in isopropanol. 11.2 g (68.6% of theory) of colorless crystals are obtained; 205-206 ° С, Calculated,%: C 55.5, H 6.1, N11, C1 14.3 (497) C1 C 55.4; H 6.2 N 11.4; Found, C1 14.0 EXAMPLE 11, 1-C3- (5-Methyl-1, 3,4-oxadiazolyl-2) -phenoxy-3-4- (3-methoxyphenyl) -piperazinyl-G - propanol-2 is prepared as in Example 1 in ethanol, the free piperazine derivative is crystallized from the reaction solution and sucked off. Obtain 10.1 g (72% of theory) of colorless crystals m.pl, 125-127 0. Calculated,%: C 65.1 H 6.6 G N13.2 (24) Found,%: C 64.9; H 6.6; N 13.3 Example 12 1-p- (5-Methyl-1,3, "I-. 4-O xadi azolyl-2) -fe-xyZ-3-4- (2-ethoxyphenyl ) -piperazinyl-13 propanol-2 was prepared as in solvent in isopropanol as in example 1. Obtain 14.6 (87% of theory) of colorless crystals t, pl, 200-202s Calculated,%; C 5b, 4; H 6, ZGM11, C; C1 13.9 NS 1 (511) 13 with 56.3. H 6, Found,: C1 13.8 Example 13. (1,3, -Oxade eolyl-2) pphenoxy-3-1h- (3-methoxyphenyl) piperazinyl-13-propanol-2 was prepared analogously to example 1 in isopropanol in as a solvent, and the free piperazine derivative is directly crystallized from the reaction solution and 12 g (98t from the theory) of colorless crystals are sucked off; m.p. 1A9-150 ° C. Calculated,%: С (, k Н 6,, N13,6% H26N404 (9) Found,%: С b ,; H 6,5 N 13, Example 14. (1,3, i-0kdiazol yl-2 -phenoxy3 - (fluorophenyl) -piperazinyl-13-propanol-2 is prepared as in solvent in isopropanol as in example 1, its own SgwHoe piperazine derivative is directly crystallized from the reaction solution and sucked off. 11.1 g (81% of theory) are obtained colorless 226-228 C. Calculated,% C 60.6, “H 6.1; NU, s, () Found,%: C 60.8; H 6, N 12.4 Except In addition, the following compounds of the invention are prepared: Example 15. (5-Methyl-1,3, -oxadiazolyl-2) -phenbxy-3-C - (3-chlorophene or) piperazinyl-P-propanol-2 (2 HCl): mp: 172-173 ° C. Example 16. 1-p-C5-Methyl-1,3, 4-oxadiazolyl-2) -phenoxy-3- G (-chlorophenyl) -piperazinyl-1,3-propanol-2 ("2 NS Ndr), mp, 21b-218 p. PRI me R 17. (1,3, + —Oxadiazolyl-2) -foxy-3-L (2; -sulfuryl) -piperazinyl-P-propanol-2 Jt, pl. 130-132C. Note E. p 18, (1, 3, -Oxadiazolyl-2) -phenoxy-3-C t (2,6-dimethylphenyl) -piperazinyl-1J-propanol-2 ("HCO, mp 222-22 C Example 19. 1-EZ- (5-Methyl-1,3, + -oxadiazolyl-2) -phenoxy-3 C (2,6-dimethylphenyl) -piperazinyl-l-nponanol-2 (“HC) Gt.pl 187-1880 C. Example 20. 1-.3- (5-Methyl-1, 3-oxydiazolyl-2) phenoxy-3 G (2, -dimethoxyphenyl fl) -niperpezinyl-1-propane nol-2 (2.5 HCCL, 5aH 0); m.-pl. 195198 .. Example 21, (1,3,1-Oxadiazolyl-2) -phenoxy-3- - Uit-AH methoxyphenyl) -piperazinyl-1j-nponanol -2, t, pl, 1i it-147 c. 100 fl, 1, 6li Example 22, 1-Сз- (1,3,4 0xadiazolyl-2) -phenoxyZ-3 - ("- phenyl-piperazinyl-1) -propanol 2, mp, 136138 ° С EXAMPLE 23 (5-Methyl-1,3, 4-oxadiazolyl-2) -phenoxy-7-3-C phenyl-piperazinyl-3-propanol-2. PRI me R. (5-Methyl-1,3 1 -oxadiazolyl-2) phenoxy3-3-C-methoxyphenyl) piperazi1 "l-11-propanol-2} T.PL. 1b6-1b8rc. Example p 25. (1,3, -Oxadiazolyl-2) -phenoxy-3C (2-methoxyphenyl) piperazinyl-1: -propanol-2 ("2) m.p. . Example 26. (t, 3, -OKca diazolyl-2) -fvnoxy-3- - (2-lorofenyl) -piperazinyl-13-propanol-2 {2 HCl); m.p. 2 9-251 ° C. PRI me R 27. (5-Methyl-1,3, -oxadiazolyl-2) -phenoxy-3- (2-methoxyphenyl) piperazinyl-J-propanol-2 (salt of oxalic acid) f so pl. 1b2-1bZ ° C. Example 28 (5-methyl-1,3, -oxadiazolyl-2) -phenoxy} -3- & (3-methoxyphenyl) piperazinyl-1gpropanol-2 (2.5 HCl) ,; m.p. 230-233 ° C. Example 29. (1,3, -Oxadiazolyl-2) -phenoxy-3-C (2, -dimethoxyphenyl) -piperazinyl-l3 nponanol-2 | m.p. . Preparations which receive in the usual way 1. Tablets containing, mg: a) The active principle of forg. . mules II) 5 Lactose200 Methylcellulose15 Cornstarch50 Talc11 Magnesium stearate k Qj Actual principle of the formula (1) 20 Lactose178 Avicel80 Polyvinyl wax 600020 Magnesium stearate 2, In The active principle of formula (I) 50 Polyvinylpyrrolidone170 Polyethylene glycol I1 40 Talc Magnesium Stearate 2 The active principle is moistened with polyvinylpyrrolidone in 10% nbm aqueous solution is forced through a sieve with openings of 1.0 mm and a height of
    权利要求:
    Claims (1)
    [1]
    Claim
    A method for producing the phenylpiperazine derivatives of 1,3,4-oxadiazolylphenol of the general formula (I) in the presence of a solvent at the boiling point of the OD reaction mixture, followed by isolation of the target product in free form or in the form of an acid addition salt.
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    GB8911158D0|1989-05-16|1989-07-05|Janssen Pharmaceutica Nv|Antiviral pyridazinamines|
    EP0533268B1|1991-09-18|2001-08-16|Glaxo Group Limited|Benzanilide derivatives as 5-HT1D antagonists|
    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    DE19803005287|DE3005287A1|1980-02-13|1980-02-13|PHENYLPIPERAZINE DERIVATIVES OF 1,3,4-OXADIAZOLYLPHENOLS, THEIR PRODUCTION AND THERAPEUTIC AGENTS CONTAINING THEM|
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