SU386507A1 - 5> & O.SIGOZ! AP - Google Patents
5> & O.SIGOZ! APInfo
- Publication number
- SU386507A1 SU386507A1 SU1670581A SU1670581A SU386507A1 SU 386507 A1 SU386507 A1 SU 386507A1 SU 1670581 A SU1670581 A SU 1670581A SU 1670581 A SU1670581 A SU 1670581A SU 386507 A1 SU386507 A1 SU 386507A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- compound
- cyanophenoxy
- optically active
- sigoz
- salts
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- MAXGKGLXEAPYGY-UHFFFAOYSA-N 2-[3-(ethylamino)-2-hydroxypropoxy]benzonitrile Chemical compound CCNCC(O)COC1=CC=CC=C1C#N MAXGKGLXEAPYGY-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- YONLFQNRGZXBBF-ZIAGYGMSSA-N (2R,3R)-2,3-dibenzoyloxybutanedioic acid Chemical compound O([C@@H](C(=O)O)[C@@H](OC(=O)C=1C=CC=CC=1)C(O)=O)C(=O)C1=CC=CC=C1 YONLFQNRGZXBBF-ZIAGYGMSSA-N 0.000 description 1
- -1 2-cyanophenoxy Chemical group 0.000 description 1
- KDPAWGWELVVRCH-UHFFFAOYSA-N Bromoacetic acid Chemical compound OC(=O)CBr KDPAWGWELVVRCH-UHFFFAOYSA-N 0.000 description 1
- XCVNDBIXFPGMIW-UHFFFAOYSA-N N-ethylpropan-1-amine Chemical class CCCNCC XCVNDBIXFPGMIW-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atoms Chemical group C* 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N oxalic acid Chemical class OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229920000346 polystyrene-polyisoprene block-polystyrene Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 230000001681 protective Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
Description
1one
Изобретение относитс к способу получени нового производного этиламинопропана, обладающего фармакологической активностью, и который в св зи с этим может найти применение в медицинской практике.The invention relates to a method for producing a new derivative of ethylaminopropane, which has pharmacological activity, and which can therefore be used in medical practice.
Способ основан на известной реакции дезацилировани аминов, однако с использованием этой реакции в изобретении получено неописанное в литературе соединение, обладающее ценными свойствами.The method is based on the known amine de-acylation reaction, however, using this reaction in the invention, a compound not described in the literature with valuable properties was obtained.
В соответствии с изобретением онисываетс способ получени 1-(2-цианфенокси)-2-окси-3-этиламинопропана формулыIn accordance with the invention, a process for the preparation of 1- (2-cyanophenoxy) -2-hydroxy-3-ethylaminopropane of the formula
С V OCHf-CHOH-CHx-NHC HsC V OCHf-CHOH-CHx-NHC Hs
или его солей, заключающийс в том, что в соединении формулыor its salts, consisting in the fact that in the compound of formula
OG ОСНг-СН-СНг-КНСгНйOG OSSNg-CH-SNG-KSNGNy
где G означает гидролитически легко отщепл емую защитную группу, например, ацильную или остаток ацетал , замещают эту группу на водород известным способом. Полученное соединение имеет асимметрический атом углерода в группировке -СПОИ и поэтому может иметь форму рацемата или оптически-активных антиподов.where G is a hydrolytically easily cleavable protecting group, for example, an acyl or acetal residue, replacing this group with hydrogen in a known manner. The resulting compound has an asymmetric carbon atom in the –PLAH group and can therefore be in the form of a racemate or optically active antipodes.
Оптически-активные соединени можно получить либо исход из оптически-активных исходных соединений, либо нутем расщеплени рацемата полученного соединени обычным образом, например с помощью дибензоилвинной или бромкамфорной кислот. Полученное соединение выдел ют или в свободном виде, или в виде кислотноаддитивных солей. Пригодными дл этих целей кислотами вл ютс , нанример, сол на , серна , бромистоводородна , метапсульфокислота, малеинова , молочна , винна и другие.The optically active compounds can be prepared either from optically active starting materials or by chipping the racemate of the resulting compound in the usual manner, for example with dibenzoyl tartaric or bromoacetic acid. The compound obtained is isolated either in free form or in the form of acid addition salts. Suitable acids for this purpose are, for example, hydrochloric, sulfuric, hydrobromic, metapsulfonic, maleic, lactic, tartaric and others.
При м е р. 1-(2-цианфенокси)-2-окси-3-этпламинопропан гидрохлорид. 1,08 г (0,03 моль)An example. 1- (2-cyanophenoxy) -2-hydroxy-3-etpaminopropane hydrochloride. 1.08 g (0.03 mol)
соли щавелевой кислоты 1-этнламино-3-(2цианофенокси ) - 2 - пропанол-тетрагидропиранилэфира раствор ют в 15 мл 1 н. НС н нагревают в течение 30 мин в кип щей вод ной бане. После охлаждени подщелачиваютoxalic acid salts of 1-ethnlamino-3- (2 cyanophenoxy) -2-propanol-tetrahydropyranyl ether are dissolved in 15 ml of 1N. HCN is heated for 30 minutes in a boiling water bath. After cooling alkalinize
20%-ным NaOH. Выпавшее основанпе поглощают хлороформом. Экстракт СИСЬ промывают Н2О, сушат MgSOi и сгущают. Остающеес основание раствор ют в спирте и подвергают кристаллизации эфиром. Выход гидрохлорида 300 мг, т. пл. 130-132°С.20% NaOH. The precipitated base is taken up in chloroform. The extract of SIS is washed with H2O, dried with MgSOi and concentrated. The remaining base is dissolved in alcohol and crystallized with ether. The output of hydrochloride 300 mg, so pl. 130-132 ° C.
Предмет изобретени Subject invention
Способ получени 1-(2-цианфенокси)-2-окси-3-этиламинопропана общей формулыThe method of obtaining 1- (2-cyanophenoxy) -2-hydroxy-3-ethylaminopropane of the general formula
CNCN
У-ОСНг-СНОН- CHg-MCgHsY-OSSg-SNON-CHg-MCgHs
или его солей, отличающийс тем, что в соединении формулыor its salts, characterized in that in the compound of formula
4 ОС4 OS
GKGK
(OCH2-CK-CH2-NHC2H.(OCH2-CK-CH2-NHC2H.
где G означает гидролитически легко отщенл емую защитную грунну, нанример цильную ,замещают эту групну на водо.род известным снособом и полученный продукт выдел ют в виде свободного соединени или соли, в виде рацемата или оптически-активных антиподов обычными приемами.where G means a hydrolytically easily peeled off protective primer, nanodimeric, replace this group with a known hydrogen and the resulting product is isolated as a free compound or salt, as a racemate or optically active antipodes by conventional methods.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1940566A DE1940566C3 (en) | 1969-08-08 | 1969-08-08 | 1- (2-Nitrilophenoxy) -2-hydroxy-3ethylaminopropane, process for its preparation and pharmaceuticals containing it |
| SU1469623A SU347996A1 (en) | 1970-07-30 | METHOD FOR OBTAINING OPTICAL |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SU386507A1 true SU386507A1 (en) | |
| SU386507A3 SU386507A3 (en) | 1973-06-14 |
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