SU493062A3 - Method for producing alkanolamine derivatives - Google Patents
Method for producing alkanolamine derivativesInfo
- Publication number
- SU493062A3 SU493062A3 SU1689989A SU1689989A SU493062A3 SU 493062 A3 SU493062 A3 SU 493062A3 SU 1689989 A SU1689989 A SU 1689989A SU 1689989 A SU1689989 A SU 1689989A SU 493062 A3 SU493062 A3 SU 493062A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- carbon atoms
- alkyl
- solution
- derivatives
- formula
- Prior art date
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
- C07D303/22—Ethers with hydroxy compounds containing no oxirane rings with monohydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
- C07C243/24—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids
- C07C243/26—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C243/30—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of an unsaturated carbon skeleton
- C07C243/32—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of an unsaturated carbon skeleton the carbon skeleton containing rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/54—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition of compounds containing doubly bound oxygen atoms, e.g. esters
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/62—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by hydrogenation of carbon-to-carbon double or triple bonds
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
- C07C45/74—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with dehydration
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/42—Unsaturated compounds containing hydroxy or O-metal groups
- C07C59/52—Unsaturated compounds containing hydroxy or O-metal groups a hydroxy or O-metal group being bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/42—Unsaturated compounds containing hydroxy or O-metal groups
- C07C59/56—Unsaturated compounds containing hydroxy or O-metal groups containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/04—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D263/06—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by oxygen atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
- C07D303/24—Ethers with hydroxy compounds containing no oxirane rings with polyhydroxy compounds
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Description
(54) СПОСОБ ПОЛУЧЕНИЯ ТРОИЗВОДНЫХ АЛКАНОЛАМИНА(54) METHOD FOR OBTAINING ALKANOLAMINE DRAIN DERIVATIVES
шуеи0й€Е581}Шshui0 € E581} W
где R « алкильный, оксиалкильный,where R "alkyl, oxyalkylene,
арилоксиалкильный, аралкИль- ный или алкенильный радикал; алкильный, галоидалкильный или алкенильный радикал, заключак. шийс во взаимодействии соедин&ни формулыaryloxyalkyl, aralkyl or alkenyl radical; alkyl, haloalkyl or alkenyl radical, concluding. Shys in the interaction of the compound &
|с амином формулы iNHjRj где it , имеет указанное значение.| with an amine of the formula iNHjRj where it, has the indicated value.
Однако в литературе отсутствуют свв .. шени о получении производных ( амина, отличающихс от йчзвестиых наличи ем замещенной аминогруппы в фениле.However, there are no references in the literature on the preparation of derivatives (of an amine, which differ from those of the presence of a substituted amino group in phenyl).
Вместе с тем указанные соединени 20 рбладакгг высокой фармакологической ак-At the same time, these compounds of 20 rbladakgg of high pharmacological ak
|ТИВНОСТЬЮ.| Tivnuyu.
Предлагаетс способ получени производных ; алканоламина обшей формулыA method for producing derivatives is proposed; alkanolamine general formula
ОСНгСНОНСИгИНИOSSNGSONGSINI
(ъ(ъ
где -апкил или оксиалкил, содержащий| до 6 углеродных атомов; 8 - водород или аминогруппа, алкил, алкенил, содержащие до 6 атомов углерода; . , -../..:where β-alkyl or oxyalkyl containing | up to 6 carbon atoms; 8 - hydrogen or amino group, alkyl, alkenyl, containing up to 6 carbon atoms; . , - .. / ..:
; Kj одинаковые или различные при irx« 2 водород, галоид, нитро-, окси-, цианогрушга , алкил, алкенил, ацил или алкоксикарбонил , содержащие до 6 углеродных; Kj are the same or different for irx "2 hydrogen, halogen, nitro, hydroxy, cyano, alkyl, alkenyl, acyl or alkoxycarbonyl, containing up to 6 carbon
КОСО -АKOSO -A
где а, S. , А иПимеют указанные значени ми- низщий алкил,.where a, s., a and i have the indicated values of lower alkyl ,.
подвергают взаимодействию с соединением формулы subjected to interaction with the compound of the formula
ГДё-Яь меет указанное значение. PeagiHjo можно проводить в среде разбавител или растворител , например в воде. Целевые продукты выдел ют известным способом в виде основани или соли...GDo-Yai has the specified value. PeagiHjo can be carried out in a diluent or solvent medium, for example in water. The desired products are isolated in a known manner as a base or salt ...
Предпочтительными сол ми производных агасаноламина вл ютс , например, сопи неорганических кислот, таких как хлор-, бромгидраты, фосфаты или сульфаты , или сопи органических кислот, например оксалаты, лактаты, тартраты, ацетаты , салипилаты, цитраты, бензоаты, -наф . тоаты, адипинаты, или 1,1-метилен-бис- - ( 2-окси - 3 -нафтоаты ), или соли кисльгх синтетических смол, например сульфи;рованных полистиролов.Preferred salts of the agasanolamine derivatives are, for example, copium inorganic acids, such as chloro, bromohydrates, phosphates or sulphates, or copi of organic acids, for example oxalates, lactates, tartrates, acetates, salipilate, citrates, benzoates, -naf. toates, adipates, or 1,1-methylene-bis- (2-hydroxy-3-naphthoates), or salts of acidic synthetic resins, for example, sulfated polystyrenes.
Пример. Раствор 0,75 г 3 изопропиламино-1-Т1-метоксикарбонилме- тилфенокси-2-пропана j в 3 мл 6 3%-ного водного раствора гидразингидрата нагревают при 95-100 С в течение 2 час. Добавл ют 20 мл воды и смесь дважды экстрагируют; по ЗО мл хлороформа. Объе диненные хлороформовые растворы сушат и выпаривают досуха, а твердый остаток перекристаллизовывают из смеси этилацетата и петролинейного эфира (т.кип. 60- -80 с). Полученный 1-«-карбазинметил- фенокси-3-изопропиламино-2-проПанол имеет т.пл. 92-03°С.Example. A solution of 0.75 g of 3 isopropylamino-1-T1-methoxycarbonylmethylphenoxy-2-propane j in 3 ml of 6 3% aqueous hydrazine hydrate solution is heated at 95-100 ° C for 2 hours. 20 ml of water are added and the mixture is extracted twice; on 30 ml of chloroform. The combined chloroform solutions are dried and evaporated to dryness, and the solid residue is recrystallized from a mixture of ethyl acetate and petroline ether (bp 60-80 sec). The resulting 1 - “- carbazinmethyl-phenoxy-3-isopropylamino-2-pro-propanol has so pl. 92-03 ° C.
атомов, алкилтио-, алкокси-, алкенилоксигруппы , содержащие до 5 углеродных атомов , замещенные по крайней мере, одной окси- или алкоксигруппами, содержащими до 4 атомов углерода, или галоидамиatoms, alkylthio, alkoxy, alkenyloxy groups containing up to 5 carbon atoms, substituted by at least one hydroxy or alkoxy group containing up to 4 carbon atoms, or halogen
А - алкилвн Сл- Сдили алкенилен Cg ,Т1« 1 или 2,A - alkyls CL-Sdili alkenylene Cg, T1 "1 or 2,
или их солей, заключающийс в том, что соединение формулыor their salts, consisting in the fact that the compound of the formula
ocH CHOHCH iiiHHiocH CHOHCH iiiHHi
i- Примен емый в качестве исходногоi- Used as reference
iBemecTBa З-изопропиламино-1-Н-метоксикарбонилметилфенокси-2-пропанол может 30 быть синтезирован следующим способом. Раствор 0,5 г l-it-карбаминметилфенокси-3-изопропиламино-2-пропанола в 5 О мл метанола насыщают безводным хлористым водородом и нагревают с об35 ратным холодильником в течение 3 час. Раствор выпаривают досуха, твердый остаток раствор ют в воде, а раствор подщелачивают карбонатом натри . Цепочной раствор дважды экстрагируют хлороформом iBemecTBa 3-isopropylamino-1-H-methoxycarbonylmethylphenoxy-2-propanol can be 30 synthesized by the following method. A solution of 0.5 g of l-it-carbamine methylphenoxy-3-isopropylamino-2-propanol in 5 O ml of methanol is saturated with anhydrous hydrogen chloride and heated under reflux for 3 hours. The solution is evaporated to dryness, the solid residue is dissolved in water, and the solution is alkalinized with sodium carbonate. The chain solution is extracted twice with chloroform
40 по 30 мл, и объединенные xлopoфopмoвьfe экстракты сущат и выпаривают досуха.40 to 30 ml, and the combined chloroform extracts are dried and evaporated to dryness.
Твердый остаток перекристаллизовывают и The solid residue is recrystallized and
петролейного эфира (т.кип.- 60-8О°С). I Полученный З-изопропиламино-1-ТЬ-меток45 сикарбонилметилфенокси-2-пропанол имеет т.пл. 65-67°С.petroleum ether (t.kip.- 60-8O ° C). I The obtained 3-isopropylamino-1-TH-labels45 of sicarbonylmethylphenoxy-2-propanol has so pl. 65-67 ° C.
/ Пример 2. Суспензию 1 г l-ji50 -этоксикарбонилметилфенокси-3-изопропиламино-2-пропанола в 75 мл водного раствора аммиака (плотность 0,88) перемащивают при комнатной температуре в течение 18 час, и получающийс раствор выпарива-г ют досуха. Полученный 1г-Т11-карбаминметил55Example 2. A suspension of 1 g of l-ji50 -etoxycarbonylmethylphenoxy-3-isopropylamino-2-propanol in 75 ml of an aqueous solution of ammonia (density 0.88) is stirred at room temperature for 18 hours and the resulting solution is evaporated to dryness. Received 1g-T11-carbaminmethyl55
фенокси-3-изопропиламино-2 аропанол име-. ет т.пл. 146 148°С.phenoxy-3-isopropylamino-2 aropanol have-. em 146 148 ° C.
Примен емый в качестБе исходного 60 вещества 1-и-этоксикарбонилметилфеноксигв-из6лропиламино-2 11ропанол может быть попучен по следующей методике. ; Газообразный хлористый водород про булькиваетс в течение 6 час через ки (П щий раствор 4,5 г 1-й-цианметилфенокси в-иэопропиламинс-2- пропанолав .1.50 мл (абсолютного этанола. Раствор выдерживаThe 1-and-ethoxycarbonylmethylphenoxycv-i6-6-propylamino-2 11 propanol used as the initial 60 substance can be fed according to the following procedure. ; Gaseous hydrogen chloride bubbled for 6 hours through ki (Fugging solution of 4.5 g of 1-y-cyanmethylphenoxy-e-propylamine-2-propanol. 1.50 ml (absolute ethanol. Holding solution
.-/.- /
R NHCOCHR NHCOCH
|у-казанн1Ь1е влабл 1J| u-kazanniye1lablab 1J
- V n--i fc--wi-i..--i--..-.-. ;...-- . OCH CHOHCH2}5HBV , - V n - i fc - wi-i ..-- i --..-.-. ; ...--. OCH CHOHCH2} 5HBV,
RR
3i3i
IT.a б, л и ц a. jr ют при комнатной температуре в течение |16 час, |а-затем выпаривают. i Пример 3. Повтор ют описанную в примере 2 операцию с тем исключением, что в качестве исходных берут соответствующие 1-7фенокси-3-аминопропанол-2 и амин. Полученные соединени формулыIT.a b, l and c a. jr at room temperature for | 16 hours, | a-then evaporated. i Example 3. The operation described in example 2 is repeated with the exception that the corresponding 1-7 phenoxy-3-aminopropanol-2 and amine are taken as the starting ones. The resulting compounds of the formula
Изопропил Мётокси трет-Бутил Метокси Изопропил Изцпропил Метил 1-Метил-2Изопропил Бром Изопропил Изо пропил втор-Бутил Изопропил н-Пропил Изопропил н.-Бутил н-Бутил н-Бутил Изопропил Изопропил Метил трет-Бутил Метил Изопропил Изопропил Изопропил трет-Бутил Изопропил Изо пропил Метил трет-Бутил Изопропил н-Пропил Метил Изопропил трет-Бутил Изопропил трет-БутилIsopropyl Mötoxy tert-Butyl Methoxy Isopropyl Izpropyl Methyl 1-Methyl-2 Isopropyl Bromine Isopropyl From propyl sec From propyl Methyl tert-Butyl Isopropyl n-Propyl Methyl Isopropyl tert-Butyl Isopropyl tert-Butyl
Шолученчы . со йнени , формулы IKtNHCO-A-ffScholuchenchy. from formula IKtNHCO-A-ff
приведены в табл. 2.are given in table. 2
,Cli,-Бром, Cli, -Brom
НH
Т а б л и ц а 2Table 2
69- 71 11887126126134107 - 105 102 (кислый оксалат) 101130 (кислый оксалат) 124117 116115117 . 213 (оксалат) 211114 112108 106189 (оксалат) 18796 94- 134 132119 11787- 1191259792- 101100VoCH CHOHCHiraCHlCH ,,).69-71 11887126126134107 - 105 102 (acid oxalate) 101130 (acid oxalate) 124117 116115117. 213 (oxalate) 211114 112108 106189 (oxalate) 18796 94- 134 132119 11787-1191259792-101100VoCH CHOHCHiraCHlCH,).
оксалат)oxalate)
ИоКОСНJockin
OCH CHOHCH UHCHiCHOOCH CHOHCH UHCHiCHO
ъпbp
приведены . 3.are given. 3
Предмет изобретени Subject invention
Способ получени производных алканоламина |Обшей формулыThe method of obtaining alkanolamine derivatives | General formula
И -ЙНСО-А-/ -ocH снонсн„штAND -YNSO-A- / -ocH snones "pcs
..
. „ . „
Ц)т1P) p1
. гдё||.влкил илиоксиалкил, содержангие до 6 углеродных атомов;. where ||. alkyl or oxyalkyl, containing up to 6 carbon atoms;
Я,- водород или аминогруппа, алкил, алкенил, содержащие до 6 атомов углеги;да,I, - hydrogen or amino group, alkyl, alkenyl, containing up to 6 carbon atoms, yes,
одинаковые или различные при same or different when
Таблица 3Table 3
0, водород, галоид, нитро-, окси-, цианогруппа ,алкнл, алкенил, ацил или алкоксикарбонил , содержащие до 6 углеродных атомов, циклоалКйл, содержащий до 8 ато0, hydrogen, halo, nitro, hydroxy, cyano, alkyl, alkenyl, acyl or alkoxycarbonyl containing up to 6 carbon atoms, cycloalkyl containing up to 8 atoms
МОЕ углерода, алкилтио-, алкокси- алкейй / оксигруппы, содержащие до 5 утлеродных атомов, арил, арилоксил, аралкил, аралкокснл, содержащие до 1О углеродных атомов, алкилы, содержащие до 5MY carbon, alkylthio, alkoxy-alkey / hydroxy groups containing up to 5 carbon atoms, aryl, aryloxyl, aralkyl, aralkoksnl containing up to 1O carbon atoms, alkyls containing up to 5
углеродных атомов, замещенные, поcarbon atoms, substituted by
краййей мере, одной окси- или лкоксигруппами , содержащими до 4 атомов углерода, или галоидами;at least one hydroxy or lkoxy group containing up to 4 carbon atoms or halogens;
А - алкилен Q - С или- алкеиилен P.2-C5V вA - alkylene Q - C or - alkoxylen P.2-C5V in
99
fl,- 1 или 2,fl, - 1 or 2,
или их солей, отличающийс тем,, что соединение формулыor salts thereof, characterized in that the compound of the formula
-ОСН СНОНСН„К Н 11.-OSH SNONSN „KN 11.
, ,
имеют указанныеhave indicated
493О62493О62
10ten
1 - низший ал кил,1 - lower kil,
подвергают взаимодействию с соединением формулы subjected to interaction with the compound of the formula
гдefJJЯ eeт указанное значение, с последующим выделением целевого продукта -известным способом в виде свободного соединени или соли.where the value specified is followed, followed by isolation of the desired product by a known method in the form of a free compound or salt.
Приоритет по признаку:Priority by grounds:
от 21.О2.69 при R. - алкил или оксиалкил;from 21.O2.69 with R. - alkyl or oxyalkyl;
от 24.09.69 при А - алкилен.from 09/24/69 with A - alkylene.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB47048/69A GB1285038A (en) | 1969-02-21 | 1969-02-21 | Alkanolamine derivatives |
| GB944569 | 1969-02-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU493062A3 true SU493062A3 (en) | 1975-11-25 |
Family
ID=26242944
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU701404586K SU482943A3 (en) | 1969-02-21 | 1970-02-20 | Method for producing alkanolamine derivatives |
| SU1689989A SU493062A3 (en) | 1969-02-21 | 1970-02-20 | Method for producing alkanolamine derivatives |
| SU1690969A SU537626A3 (en) | 1969-02-21 | 1971-08-03 | Method for producing alkanolamine derivatives |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU701404586K SU482943A3 (en) | 1969-02-21 | 1970-02-20 | Method for producing alkanolamine derivatives |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1690969A SU537626A3 (en) | 1969-02-21 | 1971-08-03 | Method for producing alkanolamine derivatives |
Country Status (20)
| Country | Link |
|---|---|
| JP (2) | JPS535287B1 (en) |
| AT (3) | AT303005B (en) |
| BE (1) | BE746107A (en) |
| CA (1) | CA945172A (en) |
| CH (3) | CH547257A (en) |
| CS (3) | CS153064B2 (en) |
| DE (1) | DE2007751C2 (en) |
| DK (1) | DK135278B (en) |
| ES (1) | ES376788A1 (en) |
| FI (1) | FI53120C (en) |
| FR (1) | FR2034561A1 (en) |
| IE (1) | IE34003B1 (en) |
| IL (1) | IL33931A (en) |
| KE (1) | KE2582A (en) |
| NL (1) | NL162363C (en) |
| NO (1) | NO128653B (en) |
| PL (3) | PL87019B1 (en) |
| SE (1) | SE391517B (en) |
| SU (3) | SU482943A3 (en) |
| YU (4) | YU34275B (en) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1311521A (en) * | 1970-02-13 | 1973-03-28 | Ici Ltd | Alkanolamine derivatives |
| DE2048838A1 (en) * | 1970-10-05 | 1972-04-06 | C H Boehnnger Sohn, 6507 Ingel heim | New 1 phenoxy 2 hydroxy 3 hydroxyal kylaminopropane and process for their manufacture |
| FR2132570B1 (en) * | 1971-04-09 | 1974-08-02 | Lipha | |
| GB1387630A (en) * | 1971-05-07 | 1975-03-19 | Ici Ltd | Phenoxyalkanolamine derivatives |
| GB1433595A (en) * | 1972-07-06 | 1976-04-28 | Ici Ltd | Alkanolamine derivatives |
| DE2623314C2 (en) * | 1976-05-25 | 1984-08-02 | Hoechst Ag, 6230 Frankfurt | 1-aryloxy-2-hydroxy-3-aminopropanes, processes for their preparation and pharmaceuticals containing them |
| DE2818999A1 (en) * | 1978-04-29 | 1979-11-15 | Basf Ag | AMINO DERIVATIVES OF 3-ALKYL-5- (2-HYDROXYSTYRYL) -ISOXAZOLES |
| DE2943405A1 (en) | 1979-10-26 | 1981-05-07 | Basf Ag, 6700 Ludwigshafen | NEW AMINO DERIVATIVES OF 5- (2-HYDROXYSTYRYL) -ISOXAZOLE |
| US4593119A (en) * | 1980-11-28 | 1986-06-03 | American Hospital Supply Corporation | Method for treatment or prophylaxis of cardiac disorders |
| US4387103A (en) * | 1980-11-28 | 1983-06-07 | American Hospital Supply Corporation | Method for treatment or prophylaxis of cardiac disorders |
| JPS57105206U (en) * | 1980-12-16 | 1982-06-29 | ||
| DE3407695A1 (en) * | 1984-03-02 | 1985-09-12 | Röhm Pharma GmbH, 6108 Weiterstadt | PTERIDINE COMPOUNDS WITH PHARMACEUTICAL EFFECTIVENESS |
| DE3500761A1 (en) * | 1985-01-11 | 1986-09-04 | SOUR "PODRAVKA" OOUR "BELUPO 2", Proizvodnja kozmetičkih preparata i lijekova, Koprivnica | Process for the production of atenolol and its derivatives |
| US4971959A (en) * | 1987-04-14 | 1990-11-20 | Warner-Lambert Company | Trisubstituted phenyl analogs having activity for congestive heart failure |
| EP0673924A4 (en) * | 1992-12-10 | 1996-04-24 | Teikoku Chem Ind Co Ltd | Propionic acid derivative. |
| JP2001524114A (en) * | 1997-04-30 | 2001-11-27 | イーライ・リリー・アンド・カンパニー | Intermediates and methods in the production of benzo [b] thiophenes |
| JP5225574B2 (en) * | 2006-11-09 | 2013-07-03 | エムキュア ファーマシューティカルズ リミテッド | Improved process for the preparation of beta-blocker compounds |
| US8552036B2 (en) | 2009-01-12 | 2013-10-08 | Hetero Research Foundation | Polymorph of atazanavir sulfate |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1593762A1 (en) * | 1967-02-06 | 1972-06-08 | Boehringer Sohn Ingelheim | Process for the preparation of new substituted 1-phenoxy-2-hydroxy-3-alkylaminopropanes |
-
1970
- 1970-02-09 CA CA074,353A patent/CA945172A/en not_active Expired
- 1970-02-10 IE IE174/70A patent/IE34003B1/en unknown
- 1970-02-11 PL PL1970174450A patent/PL87019B1/en unknown
- 1970-02-11 PL PL1970138762A patent/PL77781B1/en unknown
- 1970-02-11 PL PL1970174445A patent/PL93998B1/en unknown
- 1970-02-17 BE BE746107D patent/BE746107A/en not_active IP Right Cessation
- 1970-02-18 AT AT146270A patent/AT303005B/en not_active IP Right Cessation
- 1970-02-18 CH CH232770A patent/CH547257A/en not_active IP Right Cessation
- 1970-02-18 CH CH1804972A patent/CH561175A5/xx not_active IP Right Cessation
- 1970-02-18 AT AT761571A patent/AT305244B/en not_active IP Right Cessation
- 1970-02-18 CH CH1804472A patent/CH553747A/en not_active IP Right Cessation
- 1970-02-18 AT AT762071A patent/AT305249B/en not_active IP Right Cessation
- 1970-02-19 FI FI443/70A patent/FI53120C/fi active
- 1970-02-19 DK DK81370AA patent/DK135278B/en unknown
- 1970-02-19 YU YU410/70A patent/YU34275B/en unknown
- 1970-02-19 DE DE2007751A patent/DE2007751C2/en not_active Expired
- 1970-02-19 IL IL33931A patent/IL33931A/en unknown
- 1970-02-20 FR FR7006241A patent/FR2034561A1/en active Granted
- 1970-02-20 CS CS561270*A patent/CS153064B2/en unknown
- 1970-02-20 SU SU701404586K patent/SU482943A3/en active
- 1970-02-20 JP JP1473970A patent/JPS535287B1/ja active Pending
- 1970-02-20 SE SE7002190A patent/SE391517B/en unknown
- 1970-02-20 NL NL7002414.A patent/NL162363C/en not_active IP Right Cessation
- 1970-02-20 CS CS118670A patent/CS153062B2/cs unknown
- 1970-02-20 SU SU1689989A patent/SU493062A3/en active
- 1970-02-20 NO NO00611/70A patent/NO128653B/no unknown
- 1970-02-20 CS CS561770*A patent/CS153069B2/cs unknown
- 1970-02-21 ES ES376788A patent/ES376788A1/en not_active Expired
-
1971
- 1971-08-03 SU SU1690969A patent/SU537626A3/en active
-
1973
- 1973-01-18 JP JP48008227A patent/JPS5037182B1/ja active Pending
-
1975
- 1975-06-29 YU YU1933/75A patent/YU34278B/en unknown
- 1975-07-29 YU YU1934/75A patent/YU34279B/en unknown
- 1975-07-29 YU YU1936/75A patent/YU34281B/en unknown
- 1975-11-24 KE KE2582*UA patent/KE2582A/en unknown
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