SU466681A3 - Method for preparing carbamate ketoxime derivatives - Google Patents
Method for preparing carbamate ketoxime derivativesInfo
- Publication number
- SU466681A3 SU466681A3 SU1887327A SU1887327A SU466681A3 SU 466681 A3 SU466681 A3 SU 466681A3 SU 1887327 A SU1887327 A SU 1887327A SU 1887327 A SU1887327 A SU 1887327A SU 466681 A3 SU466681 A3 SU 466681A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- lower alkyl
- general formula
- dimethyl
- preparing carbamate
- derivatives
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/18—Radicals substituted by singly bound hetero atoms other than halogen by sulfur atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Изобретение относитс к способу получени не описанных в литературе карбаматных производных кетоксимов общей формулы IThis invention relates to a process for the preparation of carbamate ketoxime derivatives of general formula I, which are not described in the literature.
ЛL
RR
, 11 411 4
В:AT:
RftJ-ti-C-xRftJ-ti-C-x
карбамил, ацил, причем низшие алкильные или алкенильные радикалы могут быть замещены X;carbamyl, acyl, the lower alkyl or alkenyl radicals being substituted by X;
Rg - водород, низший алкил, при этом Re, RD и N в группе NRsRg могут образовывать гетероциклическое кольцо.Rg is hydrogen, lower alkyl, while Re, RD and N in the group NRsRg can form a heterocyclic ring.
Известен способ получени карбаматных производных общей формулы где R, Ri, R2 и Rs имеют указанные выше значени , с последующим выделением целевого продукта известным приемом. Предлагаемый способ получени соединений общей формулы I заключаетс в том, что соединение общей формулы 0-C-N-. I II R О р I II S где Ri-RT имеют указанные выше значени ; Y - галоген, подвергают взаимодействию с соединением общей формулы НХ, где X имеет указанные выше значени , в присутствии акцептора HY, где Y имеет указанное выше значение, с последующим выделением целевого продукта известным способом. Полученные по предлагаемому способу соединени обладают высокой биологической активностью. В приведенных ниже примерах все процентные , пропорциональные и количественные соотношени вл ютс весовыми. Пример 1. 3,3-Диметил-2-метилкарбамилоксимино-1- (пирролидинил)-бутан. К раствору 12,6 г 1-бром-3,3-диметил-2-метилкарбамилоксиминобутана в 100 мл безводного эфира прикапывают 7,8 г (0,11 моль) пирролидина. Смесь перемешивают при комнатной температуре в течение 1 час и кип т т с обратным холодильником в течение 0,5 час, затем охлаждают и промывают водой . Эфирный раствор отдел ют, сушат и после удалени растворител получают 11,8 г душистого масла, которое при сто нии затвердевает в душистое вещество, т. пл. 43- 48°С. Свойства этого и аналогичных ему соединений , полученных по предлагаемому способу, приведены в таблице. Пример 2. 1-Бром-3,3-диметил-2-бутаноксим . К раствору 69 г (1,0 моль) гидроксиламипа гидрохлорида в 100 мл воды добавл ют на лед ной бане 90 г (0,5 моль) 1-бром-3,3диметил-2-бутанона . После нриливани 100 мл 95%-ного этанола смесь перемешивают в течение 16 час и затем нагревают до комнатной температуры. Полученную белую пасту фильтруют, твердый осадок промывают водой и сушат. Получают 55 г целевого соединени , т. пл. 111 -112Х. Пайдено, %: N 7,1; Вг 42,4. СбП12НВгО. Вычислено, %: N 7,1; Вг 42,4. Пример 3. 3,3-Диметил-1-нитро-2-бутаноксим . К раствору 18,2 г (0,26 моль) нитрата натри в 130 мл диметилсульфоксида добавл ют порци ми 29 г (0,15 моль) 1-бром-3,3-диметил2-бутаноноксима . Вследствие протекани слегка экзотермической реакции необходимо внешнее охлаждение дл поддержани температуры на уровне 27С. Затем, продолжа перемешивание , ввод т дополнительное количество растворител . После перемешивани в течение 20 час смесь выливают в лед ную воду и получают твердый остаток, который собирают на фильтре. Перекристаллизацией из гор чей смеси бензол-петролейный эфир 10 г твердого вещества с т. пл. 115-120 С получают 7 г белых кристаллов с т. пл. 124-125°С. Пайдено, %: С 45; Н 7,8. СбП121 20з. Вычислено, %: С 45; И 7,6. Пример 4. 3,3-Диметил-2-метилкарбамилоксимино-1-метилсульфинилбутан . Смешивают 9 г металлического натри (0,042 моль), 60 мл воды и 25 мл метанола и после охлаждени до 0°С добавл ют порци ми 8,7 г (0,04 моль) 3,3-диметил-2-метилкарбамилоксимино-1-метилтиобутана . После перемешивани при О-10°С в течение 18 час смесь нагревают до комнатной температуры, после чего упаривают летучие на ротационном испарителе , а полученный остаток экстрагируют этилацетатом. Сухой, экстракт упаривают и получают в остатке 9 г (96%) целевого соединени в виде в зкого желтого масла. Найдено, % : С 45,2; П 7,5. С9П18М2Оз5. Вычислено, %: С 46,1; П 7,7.A known method for the preparation of carbamate derivatives of the general formula wherein R, Ri, R2 and Rs are as defined above, followed by isolation of the desired product by a known procedure. The proposed method for the preparation of compounds of the general formula I is that the compound of the general formula 0-C-N-. I II R O p I II S where Ri-RT are as defined above; Y is a halogen, is reacted with a compound of the general formula HX, where X has the above values, in the presence of an acceptor HY, where Y has the above value, followed by isolation of the target product in a known manner. The compounds obtained according to the inventive method have a high biological activity. In the examples below, all percentages, proportions, and proportions are by weight. Example 1. 3,3-Dimethyl-2-methylcarbamyloximino-1- (pyrrolidinyl) -butane. To a solution of 12.6 g of 1-bromo-3,3-dimethyl-2-methylcarbamyloxy-aminobutane in 100 ml of anhydrous ether, 7.8 g (0.11 mol) of pyrrolidine are added dropwise. The mixture was stirred at room temperature for 1 hour and heated to reflux for 0.5 hour, then cooled and washed with water. The ether solution is separated, dried, and after removing the solvent, 11.8 g of fragrant oil is obtained, which, on standing, hardens into a fragrance, mp. 43-48 ° C. The properties of this and similar compounds obtained by the proposed method are shown in the table. Example 2. 1-Bromo-3,3-dimethyl-2-butanoxime. To a solution of 69 g (1.0 mol) of hydroxylamine hydrochloride in 100 ml of water is added in an ice bath 90 g (0.5 mol) of 1-bromo-3,3 dimethyl-2-butanone. After pouring 100 ml of 95% ethanol, the mixture is stirred for 16 hours and then warmed to room temperature. The resulting white paste is filtered, the solid precipitate is washed with water and dried. 55 g of the expected compound are obtained, mp. 111 -112X. Paydeno,%: N 7.1; Br 42.4. SbP12NVgO. Calculated,%: N 7.1; Br 42.4. Example 3. 3,3-Dimethyl-1-nitro-2-butanoxime. To a solution of 18.2 g (0.26 mol) of sodium nitrate in 130 ml of dimethyl sulfoxide, 29 g (0.15 mol) of 1-bromo-3,3-dimethyl2-butanone oxime were added in portions. Due to the slightly exothermic reaction, external cooling is necessary to maintain the temperature at 27 ° C. Then, continuing to stir, an additional amount of solvent is added. After stirring for 20 hours, the mixture was poured into ice-water and a solid residue was obtained, which was collected on a filter. By recrystallization from the hot benzene-petroleum ether mixture, 10 g of a solid substance with mp. 115-120 With get 7 g of white crystals with so pl. 124-125 ° C. Paideno,%: C 45; H 7.8. Sbp121 20z. Calculated,%: C 45; And 7.6. Example 4. 3,3-Dimethyl-2-methylcarbamylamino-1-methylsulfinylbutane. 9 g of metallic sodium (0.042 mol), 60 ml of water and 25 ml of methanol are mixed and after cooling to 0 ° C, 8.7 g (0.04 mol) of 3,3-dimethyl-2-methylcarbamyloxymino-1- are added in portions methylthiobutane. After stirring at 0-10 ° C for 18 hours, the mixture is warmed to room temperature, then the volatiles are evaporated on a rotary evaporator, and the resulting residue is extracted with ethyl acetate. The dry extract is evaporated to give 9 g (96%) of the desired compound as a viscous yellow oil. Found,%: C 45.2; P 7.5. S9P18M2Oz5. Calculated,%: C 46.1; P 7.7.
Предмет изобретени .The subject matter of the invention.
Способ получени карбаматпых производных кетоксимов общей формулыThe method of obtaining carbamate ketoxime derivatives of general formula
к-о-1 «KO-1 "
. f 11 . f 11
II RS кII RS to
где X -SRs, S(0)R8, SOsRs, ORs, OSOsRg, NRsRg, NOz, CN, SCN, N3 или галоген;where X is -SRs, S (0) R8, SOsRs, ORs, OSOsRg, NRsRg, NOz, CN, SCN, N3 or halogen;
Ri - водород, замещенные или незамещенные низшие алкил, алкенил, алкинил или X;Ri is hydrogen, substituted or unsubstituted lower alkyl, alkenyl, alkynyl or X;
Ra, Rs и R4 - водород, замещенные или незамещенные низщие алкил, алкенил, алкинил.Ra, Rs and R4 are hydrogen, substituted or unsubstituted lower alkyl, alkenyl, alkynyl.
причем R2 и Ra могут образовывать циклоалифатнческое кольцо;moreover, R2 and Ra can form a cycloaliphatic ring;
Rs - водород, замещенные илн незамещенные низщие алкил, алкенил, алкинил или X, причем, когда Rs и X -ORe, SRs, S(0)R8, S., NRsRg, TO Rs вместе с X образует гетероциклическое кольцо;Rs is hydrogen, substituted or unsubstituted lower alkyl, alkenyl, quinil or X, and when Rs and X -ORe, SRs, S (0) R8, S., NRsRg, TO Rs together with X forms a heterocyclic ring;
Rs и R - водород, низщие алкил, алкенил, алкииил;Rs and R are hydrogen, lower alkyl, alkenyl, alkyl;
Rs - водород, низщие алкил, алкенил, алкинил , замещенные или незамещенные арил, карбамил, ацил, причем низщие алкильные или алкенильные радикалы могут быть замещены X;Rs is hydrogen, lower alkyl, alkenyl, alkynyl, substituted or unsubstituted aryl, carbamyl, acyl, and lower alkyl or alkenyl radicals can be substituted with X;
Rg - водород, низщий алкил, при этом Rs, Rg и N в группе NRgRg могут образовывать гетероциклическое кольцо. 9 отличающийс тем, что соединение общей формулы . -D ® I II „ 1Г О о . ( II . 1 i 5 510 где Ri-R имеют вышеуказанные значени ; 10 Y - галоген; иодвергают взаимодействию с соединением общей формулы НХ, где X имеет указанные выше значени , в присутствии акцентора HY, где Y имеет указанное выше значение, с последующим выделением целевого продукта известным способом. Приоритетно признакам: 08.04.71 при X -ORg, NRaRg, CN, SCN, N02, SRg, S(O)iR8, SOaRs. 24.02.72 при X -SRs, OSOaRs, N3. Rg is hydrogen, lower alkyl, while Rs, Rg and N in the NRgRg group can form a heterocyclic ring. 9, characterized in that the compound of the general formula. -D ® I II „1Г О о. (II. 1 i 5 510 where Ri-R have the above values; 10 Y is halogen; react with a compound of the general formula HX, where X has the above values, in the presence of the HY accentor, where Y has the above value, followed by isolation of the target product in a known manner. Priority to features: 08/04/71 with X -ORg, NRaRg, CN, SCN, N02, SRg, S (O) iR8, SOaRs. 02.24.72 with X -SRs, OSOaRs, N3.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US13258471A | 1971-04-08 | 1971-04-08 | |
US229207A US3875232A (en) | 1971-04-08 | 1972-02-24 | AC Ketoxime carbamates |
Publications (1)
Publication Number | Publication Date |
---|---|
SU466681A3 true SU466681A3 (en) | 1975-04-05 |
Family
ID=26830521
Family Applications (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
SU1887327A SU466681A3 (en) | 1971-04-08 | 1972-04-07 | Method for preparing carbamate ketoxime derivatives |
SU1769624A SU454735A3 (en) | 1971-04-08 | 1972-04-07 | Method for preparing carbamate ketoxime derivatives |
SU1886513A SU466653A3 (en) | 1971-04-08 | 1972-04-07 | Method for preparing carbamate ketoxime derivatives |
Family Applications After (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
SU1769624A SU454735A3 (en) | 1971-04-08 | 1972-04-07 | Method for preparing carbamate ketoxime derivatives |
SU1886513A SU466653A3 (en) | 1971-04-08 | 1972-04-07 | Method for preparing carbamate ketoxime derivatives |
Country Status (20)
Country | Link |
---|---|
US (1) | US3875232A (en) |
JP (1) | JPS5533410B1 (en) |
AR (1) | AR192758A1 (en) |
BE (1) | BE830594Q (en) |
CA (1) | CA984399A (en) |
CH (3) | CH611275A5 (en) |
DE (1) | DE2216838C2 (en) |
EG (1) | EG10912A (en) |
ES (1) | ES401551A1 (en) |
FR (1) | FR2136055A5 (en) |
GB (1) | GB1392111A (en) |
HU (1) | HU165184B (en) |
IE (1) | IE36264B1 (en) |
IL (1) | IL39157A (en) |
IT (1) | IT954413B (en) |
NL (1) | NL175989C (en) |
PL (1) | PL89001B1 (en) |
RO (3) | RO72827A (en) |
SU (3) | SU466681A3 (en) |
YU (3) | YU39065B (en) |
Families Citing this family (28)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4215075A (en) * | 1971-04-08 | 1980-07-29 | Diamond Shamrock Corporation | Ketoxime carbamates |
US3932471A (en) * | 1972-02-24 | 1976-01-13 | Diamond Shamrock Corporation | Azide |
DE2408522A1 (en) * | 1974-02-22 | 1975-09-04 | Boehringer Mannheim Gmbh | AMINE DERIVATIVES OF AZIDOPHENOLS AND THE PROCESS FOR THEIR PRODUCTION |
US4029688A (en) * | 1974-06-27 | 1977-06-14 | Union Carbide Corporation | Carbamic pesticidal compositions |
US4018894A (en) * | 1975-01-20 | 1977-04-19 | Stauffer Chemical Company | Oxime carbonetes as fungicidal or bactericidal agents |
US3988357A (en) * | 1975-01-20 | 1976-10-26 | Stauffer Chemical Company | Certain oxime carbonates |
US4009179A (en) * | 1975-10-15 | 1977-02-22 | E. I. Du Pont De Nemours And Company | Di- and tri-substituted oxazolidin-2-one oximes |
DE2621102A1 (en) | 1976-05-10 | 1977-11-24 | Schering Ag | PROPANE-1,2-DIONE DIOXIME, SCHAEDLING KINKKKANKAGEN CONTAINING THESE COMPOUNDS AND THE PROCESS FOR THEIR PRODUCTION |
US4073930A (en) * | 1976-06-01 | 1978-02-14 | Union Carbide Corporation | Carbamoyloximes and oximes and insecticidal and miticidal compositions and methods employing them |
US4072750A (en) * | 1976-06-01 | 1978-02-07 | Union Carbide Corporation | 1,3,5-Trithiane and 1,3,5-oxadithiane carbamoyloxime compounds and insecticidal and miticidal compositions and methods employing them |
US4454134A (en) * | 1976-06-14 | 1984-06-12 | Union Carbide Corporation | Amide carbamates and amide oxime compounds |
DE2631522A1 (en) * | 1976-07-14 | 1978-01-19 | Bayer Ag | OXIME CARBAMATES OF FLUORINATED KETONES, METHOD FOR THEIR PRODUCTION AND USE AS INSECTICIDES, ACARICIDES AND NEMATICIDES |
US4045491A (en) * | 1976-10-07 | 1977-08-30 | International Flavors & Fragrances Inc. | α-Oxy(oxo) sulfides and ethers |
DE2828133A1 (en) * | 1978-06-27 | 1980-01-10 | Bayer Ag | N-SULFENYLATED CARBAMOYLOXIMINO-1-METHYLTHIO-BUTANES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS INSECTICIDES |
CA1126278A (en) * | 1978-11-09 | 1982-06-22 | Paul Winternitz | Carbamoyloximes |
US4264528A (en) * | 1978-12-04 | 1981-04-28 | Diamond Shamrock Corporation | Method of preparing ketoxime carbamates |
US4234514A (en) * | 1978-12-04 | 1980-11-18 | Diamond Shamrock Corporation | Method of preparing ketoxime carbamates |
DE2933600A1 (en) * | 1979-08-18 | 1981-04-09 | Bayer Ag, 5090 Leverkusen | SUBSTITUTED 2-CARBAMOYLOXIMINOBUTANE, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS A PEST CONTROL |
DE3125920A1 (en) | 1981-07-01 | 1983-01-20 | Basf Ag, 6700 Ludwigshafen | "METHOD FOR PRODUCING SULFIDES" |
US4387053A (en) * | 1981-11-23 | 1983-06-07 | Diamond Shamrock Corporation | Stabilization of oxime carbamates with gallic acid, lower alkyl ester derivatives thereof |
DE3204788A1 (en) * | 1982-02-11 | 1983-08-18 | Bayer Ag, 5090 Leverkusen | METHOD FOR PRODUCING 5-SUBSTITUTED 1-CHLORINE-3,3-DIMETHYLPENTAN-2-ONES |
US4640927A (en) * | 1984-03-30 | 1987-02-03 | Uniroyal Chemical Company, Inc. | Substituted oxime carbamates |
US4785108A (en) * | 1984-06-04 | 1988-11-15 | Uniroyal Chemical Company, Inc. | Substituted oxime carbamates |
US5200427A (en) * | 1984-07-27 | 1993-04-06 | The Board Of Trustees Of The Univ. Of Illinois | Porphyric insecticides |
GB2173499A (en) * | 1985-02-04 | 1986-10-15 | Ici Plc | Fungicidal dithiolopyrrolones |
US7842727B2 (en) * | 2001-03-27 | 2010-11-30 | Errant Gene Therapeutics, Llc | Histone deacetylase inhibitors |
US7214831B2 (en) * | 2002-05-22 | 2007-05-08 | Errant Gene Therapeutics, Llc | Histone deacetylase inhibitors based on alpha-chalcogenmethylcarbonyl compounds |
WO2003099272A1 (en) * | 2002-05-22 | 2003-12-04 | Errant Gene Therapeutics, Llc | Histone deacetylase inhibitors based on alpha-ketoepoxide compounds |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA846786A (en) * | 1970-07-14 | R. Baker Don. | Use of certain oxime esters in controlling fungi upon cellulosic materials | |
BE564131A (en) * | 1957-01-21 | |||
BE637723A (en) * | 1962-09-25 | |||
US3400153A (en) * | 1964-09-23 | 1968-09-03 | Union Carbide Corp | Nitroalkyl carbamoyloximes |
US3454642A (en) * | 1966-12-22 | 1969-07-08 | Upjohn Co | Alkyl 2-methylpropenyl ketoxime carbamates |
GB1214077A (en) * | 1967-11-02 | 1970-12-02 | Usv Pharma Corp | Oximes and their carbamoyl esters and the methods of preparation thereof |
NL6912150A (en) * | 1968-08-19 | 1970-02-23 | ||
US3681386A (en) * | 1969-11-06 | 1972-08-01 | Minnesota Mining & Mfg | Substituted alkanal oximes |
CH536286A (en) * | 1970-03-23 | 1973-04-30 | Agripat Sa | Process for the production of new carbamoyl oximes |
US3647861A (en) * | 1970-08-25 | 1972-03-07 | Du Pont | Substituted o-carbamylhydroxamates |
-
1972
- 1972-02-24 US US229207A patent/US3875232A/en not_active Expired - Lifetime
- 1972-03-17 CA CA137,337A patent/CA984399A/en not_active Expired
- 1972-03-27 FR FR7210622A patent/FR2136055A5/fr not_active Expired
- 1972-04-05 AR AR241311A patent/AR192758A1/en active
- 1972-04-06 EG EG138/72A patent/EG10912A/en active
- 1972-04-07 IT IT49465/72A patent/IT954413B/en active
- 1972-04-07 IL IL39157A patent/IL39157A/en unknown
- 1972-04-07 SU SU1887327A patent/SU466681A3/en active
- 1972-04-07 IE IE453/72A patent/IE36264B1/en unknown
- 1972-04-07 RO RO7282519A patent/RO72827A/en unknown
- 1972-04-07 RO RO7282518A patent/RO72853A/en unknown
- 1972-04-07 JP JP3563572A patent/JPS5533410B1/ja active Pending
- 1972-04-07 NL NLAANVRAGE7204698,A patent/NL175989C/en not_active IP Right Cessation
- 1972-04-07 YU YU00944/72A patent/YU39065B/en unknown
- 1972-04-07 ES ES401551A patent/ES401551A1/en not_active Expired
- 1972-04-07 CH CH514972A patent/CH611275A5/xx not_active IP Right Cessation
- 1972-04-07 DE DE2216838A patent/DE2216838C2/en not_active Expired
- 1972-04-07 CH CH436875A patent/CH585194A5/xx not_active IP Right Cessation
- 1972-04-07 GB GB1618772A patent/GB1392111A/en not_active Expired
- 1972-04-07 SU SU1769624A patent/SU454735A3/en active
- 1972-04-07 HU HUDI222A patent/HU165184B/hu unknown
- 1972-04-07 SU SU1886513A patent/SU466653A3/en active
- 1972-04-07 PL PL1972154659A patent/PL89001B1/en unknown
- 1972-04-07 CH CH436975A patent/CH591433A5/xx not_active IP Right Cessation
- 1972-04-07 RO RO70445A patent/RO61151A/ro unknown
-
1975
- 1975-06-24 BE BE157643A patent/BE830594Q/en not_active IP Right Cessation
-
1979
- 1979-02-12 YU YU316/79A patent/YU42298B/en unknown
- 1979-02-12 YU YU00315/79A patent/YU39102B/en unknown
Also Published As
Publication number | Publication date |
---|---|
HU165184B (en) | 1974-07-27 |
RO72827A (en) | 1982-10-11 |
CH611275A5 (en) | 1979-05-31 |
FR2136055A5 (en) | 1972-12-22 |
IT954413B (en) | 1973-08-30 |
ES401551A1 (en) | 1975-10-01 |
IE36264L (en) | 1972-10-08 |
IE36264B1 (en) | 1976-09-29 |
EG10912A (en) | 1976-12-31 |
IL39157A0 (en) | 1972-06-28 |
RO61151A (en) | 1976-10-15 |
DE2216838C2 (en) | 1985-05-09 |
IL39157A (en) | 1976-08-31 |
CA984399A (en) | 1976-02-24 |
RO72853A (en) | 1982-02-26 |
SU466653A3 (en) | 1975-04-05 |
YU31579A (en) | 1982-06-30 |
GB1392111A (en) | 1975-04-30 |
PL89001B1 (en) | 1976-10-30 |
BE830594Q (en) | 1975-10-16 |
CH591433A5 (en) | 1977-09-15 |
DE2216838A1 (en) | 1972-11-02 |
JPS5533410B1 (en) | 1980-08-30 |
NL7204698A (en) | 1972-10-10 |
AR192758A1 (en) | 1973-03-14 |
YU39065B (en) | 1984-04-30 |
US3875232A (en) | 1975-04-01 |
SU454735A3 (en) | 1974-12-25 |
CH585194A5 (en) | 1977-02-28 |
NL175989C (en) | 1985-02-01 |
NL175989B (en) | 1984-09-03 |
YU42298B (en) | 1988-08-31 |
YU94472A (en) | 1982-05-31 |
YU39102B (en) | 1984-04-30 |
YU31679A (en) | 1982-05-31 |
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