SU537625A3 - Способ получени производных 1,1-диаминоэтилена - Google Patents
Способ получени производных 1,1-диаминоэтиленаInfo
- Publication number
- SU537625A3 SU537625A3 SU2025129A SU2025129A SU537625A3 SU 537625 A3 SU537625 A3 SU 537625A3 SU 2025129 A SU2025129 A SU 2025129A SU 2025129 A SU2025129 A SU 2025129A SU 537625 A3 SU537625 A3 SU 537625A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- formula
- producing
- compound
- ethylene derivatives
- methyl
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/32—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/08—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
- C07D275/02—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/28—Radicals substituted by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/08—1,2,4-Thiadiazoles; Hydrogenated 1,2,4-thiadiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
- C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
- C07D285/135—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Description
(54) СПОСОБ ПОЛУЧЕНИЯ ПРОИЗВОДНЫХ 1,1-ДИАМИНОЭТИЛЕНА
где В представл ет собой , RNH или
RWH;
R представл ет собой
Het-(СНг)™-Z-(СН2)гг;
X, Y, R, Het, Z, т и п имеют указанные выше значени ;
Q представл ет собой серу или кислород;
R2 представл ет собой низший алкил или аралкил, подвергают взаимодействию с амином формулы RNH2 или RNH2, при условии, что если В - это RiNH, то используют амин формзлы , если В - это RNH, то используют амин формулы R:NH2, а если В - это QR-, то берут два эквивалента амина формулы .
Исходным веидеством вл етс соединение формулы II, где В - QW,
Q - кислород или сера, преимущественно сера;
R - низший алкил или аралкил, преимуш ,ественно метил. Это соединение при взаимодействии с одним эквивалентом RWH2 или RNHs приводит к соединени м формзлы II (В-RNH или RNH соответственно), которые далее, взаимодейству с эквивалентом RNH2 или R1NH2 привод т к получению соединений формулы I. В тех случа х, когда R и R имеют одинаковое значение, реакцию можио вести в одну стадию взаимодействием соединени формулы II (В-QR) с двум эквивалентами RNHa с получением целевого продукта. Описанные реакции можно вести в соответствуюш ,ем растворителе или, особенно когда , без растворител при умеренно повышенной температуре, например при 90-150°С.
Соединение формулы II (В-QR а Q-сера ) можно получить из замещенного метана формзлы CH2XY, где X и Y имеют значени , указанные выше, обработкой его сильным основанием , таким как гидрид натри или гидроокись натри и взаимодействием с сероуглеродом , и далее обработкой выделенного промежуточного продукта соединением формулы , где R имеет указанные выше значени , а Hal представл ет собой галоген.
Другой метод получени соединени II (В-QR, Q-S) заключаетс в том, что замещенный метай формулы CH2XY после обработки сильным основанием, таким как гидрид натри или гидроокись натри , подвергают взаимодействию с соединением формулы I. S, где R представл ет собой низший алкил, и далее, полученный про.межуточный продукт подвергают взаимодействию с соединением формулы .
Соединение формулы I, где R представл ет собой водород, X представл ет собой SO2Ar и Y - водород, согласно изобретению, можно получить следующим образом.
Арилсульфонилацетонитрилформулы
NCCH2S02Ar в безводной среде подвергают взаимодействию с этиловым спиртом и хлористым водородом, полученный имииоэфир формулы С2Н50-C(NH)-CH2SO2Ar ири обработке его основанием и взаимодействии с амином ф.ормулы RNH2, где R имеет зказаниое выше значение, дает целевой продукт формулы RiNHC(H2)CHSO2Ar. Пример 1. 1,1-дициан-2-метиламино-2- 2 (4-метил - 5 - имндазолил - метилтио)-этиламино -этилен .
Метод А. Гидрид цатри (50%-на масл на дисперси , 9,6 г) добавл ют к раствору иитрила малоновой кислоты (13,21 г) в сухом диметилформамиде (150 мл). Смесь перемешивают при 0°С в течение 10 мин, затем к ней по капл м добавл ют раствор метилиодида (28,4 г) в диметилформамиде (35 мл).
Реакционную смесь интенсивно перемешивают в течение 20 минут, затем ее выливают на колотый лед (500 мл). Сырой (26 г, т. ил. 115°С) продукт отфильтровывают и смывают гор чей месью этанол-эфир (3:1, 600 мл).
После фильтровани и охлаждени получают 1,1 - дициано-2-метилтио-2-метиламиноэтилен с т. пл. 119-120°С. Перекристаллизаци из воды дает образец с т. пл. 120-121°С.
Найдено, %: С 46,7; Н 4,6; N 27,1; S 20,8.
CeHrNsS.
Вычислено, %: С 47,0; Н 4,4; :N 27,4; S 20,9%.
К перемешиваемой суспензии 4-метнл-5-(2аминоэтил ) - тиометилимидазола (1,71 г) в
сухом ацетонитриле (30 мл) добавл ют 1,1дициано-2-метилтио - 2 - метиламиноэтилен (1,53 г). Смесь перемешивают при комнатной температуре в течение 1 час и собирают сырой продукт (1,36 г). После перекристаллизации из кип щей воды получают 1,1-дициаио-2-метиламино - 2 - 4-метил-(5-имидазолил )-метилтиоэтиламино - этилен с т. ил.
122135°С
Найдено, %: С 52,4; Н 5,8; N 30,5; S 11,6.
С,2Н1бКб5.
Вычислено, О/о: С 52,3; Н 5,8; iN 30,4; S 11,6.
Метод В. Смесь 1,1-дициано - 2 - этокси2 - метиламиноэтилена (2,27 г) и 4-метил5 - (2 - аминоэтил)-тиометил - имидазола
(2,57 г) в ацетонитриле (25 мл) перемешивают при комнатной температуре в течение 23 час. Затем реакционную смесь выиарили досуха и оставшеес масло хроматографируют на силикагеле, элюироваиие ведут с помощью
ацетона; после отгонки растворител получают 1,1 - дициано-2-метилам«но-2- {2-(4-метил-5-имидазолил ) - .метилтио} - этиламино этилеп с т. пл. 131 -133°С. Пример 2. 1 - Нитро-2-метиламино-2- 2 (2 - пиридилметилтио) - этиламино -этилеи. Раствор 2-(2 - амииоэтил) - тиометил пиридина (5,0 г ) и 1-иитро-2,2-бисметилтиоэтилена (5,28 г) в этаноле кип т т с обратным холодильником в течение 3 час. Выпаривание и хроматографическа очнстка продукта иа колонке с силикагелем с элюированием смесью изопропилового спирта и этилацетата (1:5) дает 1-иитро-2- метилтио-2-(2)-2-ииридилметилтио - этилампноэтилен (2,49 г) с
т. пл. 95,6-96,5Т.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB2356873A GB1421792A (en) | 1973-05-17 | 1973-05-17 | Heterocyclic substituted-1, 1-diamino-ethylene derivatives methods for their preparation and compositions containing them |
Publications (1)
Publication Number | Publication Date |
---|---|
SU537625A3 true SU537625A3 (ru) | 1976-11-30 |
Family
ID=10197791
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
SU2025129A SU537625A3 (ru) | 1973-05-17 | 1974-05-16 | Способ получени производных 1,1-диаминоэтилена |
Country Status (29)
Country | Link |
---|---|
US (3) | US3953460A (ru) |
JP (1) | JPS5040560A (ru) |
AR (1) | AR213262A1 (ru) |
AT (1) | AT334362B (ru) |
BE (1) | BE814941A (ru) |
BG (1) | BG25786A3 (ru) |
CA (1) | CA1050551A (ru) |
CS (1) | CS185654B2 (ru) |
DD (1) | DD113896A5 (ru) |
DE (1) | DE2423813A1 (ru) |
ES (1) | ES426405A1 (ru) |
FI (1) | FI151974A (ru) |
FR (1) | FR2229417B1 (ru) |
GB (1) | GB1421792A (ru) |
HU (1) | HU172300B (ru) |
IE (1) | IE39435B1 (ru) |
IL (1) | IL44752A (ru) |
IN (1) | IN141252B (ru) |
LU (1) | LU70104A1 (ru) |
MW (1) | MW1774A1 (ru) |
NL (1) | NL7406660A (ru) |
NO (1) | NO141407C (ru) |
PH (1) | PH11040A (ru) |
PL (1) | PL102353B1 (ru) |
RO (1) | RO69780A (ru) |
SE (1) | SE416049B (ru) |
SU (1) | SU537625A3 (ru) |
ZA (1) | ZA742650B (ru) |
ZM (1) | ZM7374A1 (ru) |
Families Citing this family (41)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1554153A (en) * | 1975-05-15 | 1979-10-17 | Smith Kline French Lab | Process for making 2-amino-2-alkylthionitroethylenes |
IL49528A (en) * | 1975-05-21 | 1980-11-30 | Smith Kline French Lab | Imidazolyl(or thiazolyl)methylthio(or butyl)guanidine or thiourea derivatives,their preparation and pharmaceutical compositions comprising them |
US4192879A (en) * | 1975-05-21 | 1980-03-11 | Smith Kline & French Laboratories Limited | Imidazolyl alkylamino nitroethylene compounds |
GB1564502A (en) * | 1975-07-31 | 1980-04-10 | Smith Kline French Lab | Guanidines thioureas and 1,1-diamino-2-nitroethylene derivatives |
US4169855A (en) * | 1976-08-04 | 1979-10-02 | Allen & Hansbury, Limited | N'-derivatives of n-(2-mercapto-ethyl)-2-nitro-1,1-ethenediamine |
GB1565966A (en) | 1976-08-04 | 1980-04-23 | Allen & Hanburys Ltd | Aminoalkyl furan derivatives |
US4165378A (en) | 1977-04-20 | 1979-08-21 | Ici Americas Inc. | Guanidine derivatives of imidazoles and thiazoles |
GR62452B (en) | 1977-04-20 | 1979-04-12 | Ici Ltd | Preparation process of guanidine derivatives |
US4153704A (en) * | 1977-05-16 | 1979-05-08 | Smith Kline & French Laboratories Limited | Ethylene derivatives |
IE46886B1 (en) * | 1977-05-17 | 1983-10-19 | Allen & Hanburys Ltd | Aminoalkyl-benzene derivatives |
GB1601459A (en) * | 1977-05-17 | 1981-10-28 | Allen & Hanburys Ltd | Aminoalkyl thiophene derivatives |
US4233302A (en) * | 1977-12-23 | 1980-11-11 | Glaxo Group Limited | Amine derivatives and pharmaceutical compositions containing them |
DE2963363D1 (en) | 1978-05-24 | 1982-09-09 | Ici Plc | Antisecretory thiadiazole derivatives, processes for their manufacture and pharmaceutical compositions containing them |
US4584384A (en) * | 1978-05-30 | 1986-04-22 | Smith Kline & French Laboratories Limited | Nitro pyrroles |
IL57415A (en) * | 1978-05-30 | 1984-08-31 | Smith Kline French Lab | Nitropyrrole compounds,process for preparing them and pharmaceutical compositions containing them |
IL57416A (en) * | 1978-05-30 | 1983-03-31 | Smith Kline French Lab | Nitro compounds,processes for preparing them and compositions containing them |
US4221737A (en) | 1978-09-26 | 1980-09-09 | Bristol-Myers Company | 1-(Alkynyl)amino-1-(mercaptoalkyl)amino ethylenes |
US4200760A (en) * | 1978-09-26 | 1980-04-29 | Bristol-Myers Company | Imidazolylalkylthioalkylamino-ethylene derivatives |
US4289876A (en) * | 1978-11-24 | 1981-09-15 | Bristol-Myers Company | Antisecretory agents |
US4250316A (en) * | 1978-11-24 | 1981-02-10 | Bristol-Myers Company | Pyridyl guanidine anti-ulcer agents |
US4282363A (en) * | 1978-11-24 | 1981-08-04 | Bristol-Myers Company | 1-Nitro-2-(2-alkynylamino)-2-[(2-pyridylmethylthio)-ethylamino]ethylene derivatives |
US4200578A (en) | 1978-12-18 | 1980-04-29 | Bristol-Myers Company | Thiazole derivatives |
NL8000869A (nl) * | 1979-02-16 | 1980-08-19 | Eisai Co Ltd | Cyanoguanidine-derivaten en werkwijze voor de bereiding daarvan. |
US4220654A (en) * | 1979-06-04 | 1980-09-02 | Merck & Co., Inc. | Cyclic imidazole cyanoguanidines |
FI803127L (fi) * | 1979-10-03 | 1981-04-04 | Glaxo Group Ltd | Heterocykliska foereningar |
US4375547A (en) * | 1980-10-02 | 1983-03-01 | Eli Lilly And Company | N-Methyl-N'-2-([(2-dimethylaminomethyl)-4-thiazolyl]methylthio)ethyl 2-nitro-1,1-ethenediamine |
US4382090A (en) * | 1980-10-02 | 1983-05-03 | Eli Lilly And Company | N-Thiazolylmethylthioalkyl-N'alkylamidines and related compounds |
US4525477A (en) * | 1981-12-02 | 1985-06-25 | Smith Kline & French Laboratories Limited | 2-Thiazolyl, isothiazolyl, oxazolyl and isoxazolyl alkylamino-3-nitro-heterocyclic compounds |
NZ202797A (en) * | 1981-12-28 | 1985-08-30 | Lilly Co Eli | Pyrimidine derivatives and pharmaceutical compositions |
DE3232462A1 (de) * | 1982-09-01 | 1984-03-01 | Bayer Ag, 5090 Leverkusen | 2-nitro-1,1-ethendiamine, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
AU2222083A (en) * | 1982-12-14 | 1984-06-21 | Smith Kline & French Laboratories Limited | Pyridine derivatives |
GB8415254D0 (en) * | 1984-06-15 | 1984-07-18 | Glaxo Group Ltd | Amine derivatives |
DE3546858C2 (de) * | 1984-06-15 | 1995-04-20 | Glaxo Group Ltd | Verfahren zur Herstellung von Ranitidin |
JPH085859B2 (ja) * | 1986-07-01 | 1996-01-24 | 日本バイエルアグロケム株式会社 | 新規アルキレンジアミン類 |
ES2053462T3 (es) * | 1987-04-06 | 1994-08-01 | Heumann Pharma Gmbh & Co | Procedimiento para la produccion de derivados de nitroetano. |
JP2001523220A (ja) * | 1996-08-06 | 2001-11-20 | スミスクライン・ビーチャム・コーポレイション | Il―8受容体アンタゴニスト |
US5955548A (en) * | 1997-05-07 | 1999-09-21 | Novo Nordisk A/S | Substituted 3, 3-diamino-2-propenenitriles, their preparation and use |
AU7331098A (en) * | 1997-05-07 | 1998-11-27 | Novo Nordisk A/S | Substituted 3,3-diamino-2-propenenitriles, their preparation and use |
GB9715814D0 (en) | 1997-07-25 | 1997-10-01 | Black James Foundation | Histamine H3 receptor ligands |
GB2344588B (en) * | 1997-07-25 | 2001-11-14 | Black James Foundation | 1H-4(5)-substituted imidazole derivatives their preparation and their use as histamine H 3 receptor ligands |
KR100302348B1 (ko) * | 1999-04-24 | 2001-09-22 | 류덕희 | 니자티딘의 제조방법 |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1078569A (en) * | 1962-12-06 | 1967-08-09 | Gen Aniline & Film Corp | Improvements in or relating to cyanoethylene compounds |
US3404159A (en) * | 1966-12-19 | 1968-10-01 | Gaf Corp | Bis hetero methylene malononitriles |
BE758146A (fr) * | 1969-10-29 | 1971-04-28 | Smith Kline French Lab | Derives de l'amidine |
US3808336A (en) * | 1970-06-25 | 1974-04-30 | Smithkline Corp | Pharmaceutical compositions and methods of inhibiting histamine activity with thiourea derivatives |
US3734924A (en) * | 1970-10-14 | 1973-05-22 | Smith Kline French Lab | Carboxamidines |
US3905984A (en) * | 1971-03-09 | 1975-09-16 | Smith Kline French Lab | Pyridyl substituted thioalkyl-and oxyalkyl-thioureas and ureas |
GB1338169A (en) * | 1971-03-09 | 1973-11-21 | Smith Kline French Lab | Ureas thioureas and guanidines |
GB1397436A (en) * | 1972-09-05 | 1975-06-11 | Smith Kline French Lab | Heterocyclic n-cyanoguinidines |
-
1973
- 1973-05-17 GB GB2356873A patent/GB1421792A/en not_active Expired
-
1974
- 1974-04-23 IN IN916/CAL/74A patent/IN141252B/en unknown
- 1974-04-25 ZA ZA00742650A patent/ZA742650B/xx unknown
- 1974-04-30 MW MW17/74*UA patent/MW1774A1/xx unknown
- 1974-05-02 IL IL44752A patent/IL44752A/xx unknown
- 1974-05-06 PL PL1974171110A patent/PL102353B1/pl unknown
- 1974-05-06 ZM ZM73/74A patent/ZM7374A1/xx unknown
- 1974-05-09 US US05/468,617 patent/US3953460A/en not_active Expired - Lifetime
- 1974-05-10 PH PH15821A patent/PH11040A/en unknown
- 1974-05-13 AT AT392974A patent/AT334362B/de not_active IP Right Cessation
- 1974-05-13 BE BE144247A patent/BE814941A/xx not_active IP Right Cessation
- 1974-05-15 DD DD178521A patent/DD113896A5/xx unknown
- 1974-05-15 CS CS7400003473A patent/CS185654B2/cs unknown
- 1974-05-15 SE SE7406472A patent/SE416049B/sv not_active IP Right Cessation
- 1974-05-16 FI FI1519/74A patent/FI151974A/fi unknown
- 1974-05-16 DE DE2423813A patent/DE2423813A1/de not_active Withdrawn
- 1974-05-16 HU HU74SI00001406A patent/HU172300B/hu unknown
- 1974-05-16 LU LU70104A patent/LU70104A1/xx unknown
- 1974-05-16 SU SU2025129A patent/SU537625A3/ru active
- 1974-05-16 NO NO741815A patent/NO141407C/no unknown
- 1974-05-16 JP JP49055300A patent/JPS5040560A/ja active Pending
- 1974-05-16 CA CA200,137A patent/CA1050551A/en not_active Expired
- 1974-05-17 RO RO7478828A patent/RO69780A/ro unknown
- 1974-05-17 AR AR253803A patent/AR213262A1/es active
- 1974-05-17 IE IE1052/74A patent/IE39435B1/xx unknown
- 1974-05-17 BG BG7400026720A patent/BG25786A3/xx unknown
- 1974-05-17 FR FR7417347A patent/FR2229417B1/fr not_active Expired
- 1974-05-17 ES ES426405A patent/ES426405A1/es not_active Expired
- 1974-05-17 NL NL7406660A patent/NL7406660A/xx not_active Application Discontinuation
-
1980
- 1980-02-04 US US06/117,901 patent/US4317829A/en not_active Expired - Lifetime
- 1980-02-04 US US06/117,903 patent/US4284640A/en not_active Expired - Lifetime
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