SU475764A3 - The method of obtaining ureidophenoxy2-hydroxy-3-aminopropanes - Google Patents

The method of obtaining ureidophenoxy2-hydroxy-3-aminopropanes

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Publication number
SU475764A3
SU475764A3 SU1779647A SU1779647A SU475764A3 SU 475764 A3 SU475764 A3 SU 475764A3 SU 1779647 A SU1779647 A SU 1779647A SU 1779647 A SU1779647 A SU 1779647A SU 475764 A3 SU475764 A3 SU 475764A3
Authority
SU
USSR - Soviet Union
Prior art keywords
hydroxy
aminopropanes
obtaining
residue
formula
Prior art date
Application number
SU1779647A
Other languages
Russian (ru)
Inventor
Вильгельм Макс
Original Assignee
Циба-Гейги А.Г. (Фирма)
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Циба-Гейги А.Г. (Фирма) filed Critical Циба-Гейги А.Г. (Фирма)
Application granted granted Critical
Publication of SU475764A3 publication Critical patent/SU475764A3/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C275/32—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms
    • C07C275/34—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms having nitrogen atoms of urea groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Description

С VO-Cib-CII-Cl: - . . 11СОС-КиА.л.,У . где Кз II Ri имеют указанные значени , с амнно .м ooHieii формулы Ri-NH-R2, где Ri н Rs имеют указанные значени . Производными такой карбамнновон кнслоты  вл етс , например, ннзшнй алкиловый сложный зфнр НЛП феннловый сложный эфир, галогенагндрнд кнслоты, нанример хлорангидрнд кнслоты нлн изоцнанат. Реакцню нровод т в нзбытке амнна н в соответствуюи1 ,ем растворителе, при повышенной температуре, обычно выше 100°С. Целевые нродукты выдел ют в свободном виде, в внде соли, рацемата нлн оптически активного изомера. Пример 1. Раствор из 15 г 1-(/г-этокспкарбоннламп1юфеиоксп )-2-окси-3 - пзопроппламинонропапа н 5 г днметиламнна в 100 мл этанола нагревают с закрытом сосуде в течение 4 час до . Потом выпаривают в вакууме досуха н остаток нерекрнсталлизовывают нз бензола. Получают (N, Н-днметилурендо)-феноксн -2-оксн-3-нзонроннлам11НОпронан форОЕ I (CHgj JrCONH OCHpCHCHaAliCH плав щийс  после перекристаллизации из бейзола при 138 139°С. По примеру 1 получают следующие соединени : 1- о-хлор-л- (N, N-диметилуреидо) -фенокси -2-окси-З-изоироииламииоироиап; т. пл. 130°С; 1 - о-аллил-п- (N, N-дпметилуреидо) -феиокси -2-окси-3-изопрош1ламииопропап; т. ил. 110-112°С; -..- (N, К-диметилуреидо) -фенокси -2-окси-З-изопроинламинопропан; т. пл. 130°С; (N-метнлурендо) - фенокс -2-оксн-3пзоироллламннопропан; т. нл. . П р е д мет ;i з о б р е т е н н   Способ НОЛучени  уреидофеноксн-2-оксн-3-a n i oпpoIlaнoв оби1;ей формулы Vo-rHj-Cti-CPrNll-R., где Ri - водород, замещенный илп пезамен 1 ,енный алифатический остаток; - замеш,енный или незамещенный алифатический остаток «ли Ri и R2 вместе означают двухвалеитный алифатический остаток , который может содерж:ать гетероатом; RS -алифатический пли циклоалифатический остаток; ( - водород, низший алкил, иизший алкенил , низший алкпппл, цпклоалкил, фенилнизший алкпл, низший алкок сил, фепил, низгиий алкенил-оксил, низший алкинилоксил, галоген , замещенный иизший алкпл, фенокси-, трифторметил- или цианогруппа, причем уреидоостаток находитс  в мета- или пара-положении по отношению к Ra - остатку, илп их солей , отличающийс  тем, что реакционноспособное ироизводное карбаминовой кислоты формулы -O-OH CII-CIirNK-Rs НООС-ЙН где RS и R4 имеют указ-анные зпачепп , подвергают взаимодействию с амином общей формулы RI-NH-R2, где RI и R2 имеют указанные значени , с последующим выделением целевого продукта в свободном виде или в виде соли, рацемата или оптически активного нзомера .With VO-Cib-CII-Cl: -. . 11COS-KiAl., U. where Cs II Ri has the indicated values, with amn omOiHieii of the formula Ri-NH-R2, where Ri n Rs have the indicated values. Derivatives of such a carbamnova acid are, for example, the alkyl alkeneous complex of the NLP, phenyl ester, halogenated agglomerates, and the acid chloride of the nl isocyanate. The reaction is carried out in the bottleneck in an appropriate solvent at an elevated temperature, usually above 100 ° C. The desired products were isolated in free form, as a salt, in the racemate and the optically active isomer. Example 1. A solution of 15 g of 1 - (/ g-ethoxpcarbonlamp1 ufeioksp) -2-hydroxy-3 - pzoproplaminonoprop n 5 g of dimethyl amine in 100 ml of ethanol is heated with a closed vessel for 4 hours to. It is then evaporated in vacuo to dryness and the residue is not rectified by ns benzene. (N, N-dnmethylurendo) -phenox-2-ox-3-nzonronl-11Nopronane I (CHyj JrCONH OCHpCHCHaAliCH melting after recrystallization from baseol at 138,139 ° C is obtained. In Example 1, the following compounds are obtained: 1-o-chloro-l - (N, N-dimethylureido) -phenoxy -2-hydroxy-3-iso-iryl-iamio-iio-iop; m.p. -isoprosh1lamioprop; t. il., 110-112 ° C .; -... (N, K-dimethylureido) -phenoxy -2-hydroxy-3-isopropylaminopropane; mp. 130 ° C .; (N-metnlurendo) -phenox -2-oxn-3pzoirollaminnopropane; so nl. Predymet; i z o bre n e n Method for the treatment of ureidopheno ksn-2-oxn-3-ani opropylanov obi1, it has the formula Vo-rHj-Cti-CPrNll-r., where Ri is hydrogen, substituted ilp pezamen 1, enen aliphatic residue, - mixed, or unsubstituted aliphatic residue "whether Ri and R 2 together means a two-valeic aliphatic residue which may contain: heteroatom; RS-aliphatic or cyclo-aliphatic residue; , lower alkynyloxy, halogen, substituted lower alkyl, phenoxy, trifluoromethyl- or c ian group, the ureido residue is in the meta or para position with respect to the Ra residue, or their salts, characterized in that the reactive and carbamic acid derivative of the formula -O-OH CII-CIirNK-Rs HOOC-JH where RS and R4 have a decree the capped compounds are reacted with an amine of the general formula RI-NH-R2, where RI and R2 have the indicated meanings, followed by isolation of the target product in free form or as a salt, racemate, or optically active nucleoside.

SU1779647A 1970-01-08 1971-01-06 The method of obtaining ureidophenoxy2-hydroxy-3-aminopropanes SU475764A3 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH20470A CH554311A (en) 1970-01-08 1970-01-08 Cardioactive amines

Publications (1)

Publication Number Publication Date
SU475764A3 true SU475764A3 (en) 1975-06-30

Family

ID=4181620

Family Applications (6)

Application Number Title Priority Date Filing Date
SU1779647A SU475764A3 (en) 1970-01-08 1971-01-06 The method of obtaining ureidophenoxy2-hydroxy-3-aminopropanes
SU1778353A SU474972A3 (en) 1970-01-08 1971-01-06 The method of obtaining ureidophenoxy-2-oxy3 aminopropanes
SU1778352A SU450397A3 (en) 1970-01-08 1971-01-06 The method of obtaining ureidophenoxy2-hydroxy-3-aminopropanes
SU1607281A SU420171A3 (en) 1970-01-08 1971-01-06 METHOD OF OBTAINING NONSATURATED AMINES
SU7201778543A SU563911A3 (en) 1970-01-08 1972-04-28 Method of producing ureidophenoxy-2-hydroxy-3-aminopropanes
SU7201778355A SU578861A3 (en) 1970-01-08 1972-04-28 Method of preparing ureidophenoxy-2-oxy-3-aminopropanes

Family Applications After (5)

Application Number Title Priority Date Filing Date
SU1778353A SU474972A3 (en) 1970-01-08 1971-01-06 The method of obtaining ureidophenoxy-2-oxy3 aminopropanes
SU1778352A SU450397A3 (en) 1970-01-08 1971-01-06 The method of obtaining ureidophenoxy2-hydroxy-3-aminopropanes
SU1607281A SU420171A3 (en) 1970-01-08 1971-01-06 METHOD OF OBTAINING NONSATURATED AMINES
SU7201778543A SU563911A3 (en) 1970-01-08 1972-04-28 Method of producing ureidophenoxy-2-hydroxy-3-aminopropanes
SU7201778355A SU578861A3 (en) 1970-01-08 1972-04-28 Method of preparing ureidophenoxy-2-oxy-3-aminopropanes

Country Status (4)

Country Link
CH (1) CH554311A (en)
PL (2) PL94162B1 (en)
SU (6) SU475764A3 (en)
ZA (1) ZA708599B (en)

Also Published As

Publication number Publication date
SU474972A3 (en) 1975-06-25
CH554311A (en) 1974-09-30
SU450397A3 (en) 1974-11-15
ZA708599B (en) 1971-09-29
SU420171A3 (en) 1974-03-15
SU563911A3 (en) 1977-06-30
PL94154B1 (en) 1977-07-30
PL94162B1 (en) 1977-07-30
SU578861A3 (en) 1977-10-30

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