SU556728A3 - The method of obtaining 2- (α-aminophenylimino) -3-aza-1-thiacycloalkanes or their salts - Google Patents

The method of obtaining 2- (α-aminophenylimino) -3-aza-1-thiacycloalkanes or their salts

Info

Publication number
SU556728A3
SU556728A3 SU1827228A SU1827228A SU556728A3 SU 556728 A3 SU556728 A3 SU 556728A3 SU 1827228 A SU1827228 A SU 1827228A SU 1827228 A SU1827228 A SU 1827228A SU 556728 A3 SU556728 A3 SU 556728A3
Authority
SU
USSR - Soviet Union
Prior art keywords
carbon atoms
salts
alkyl
formula
thiacycloalkanes
Prior art date
Application number
SU1827228A
Other languages
Russian (ru)
Inventor
Воллвебер Гартмунд
Флукке Винфрид
Петер Шульц Ганс
Томас Герберт
Original Assignee
Байер Аг (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 Байер Аг (Фирма) filed Critical Байер Аг (Фирма)
Application granted granted Critical
Publication of SU556728A3 publication Critical patent/SU556728A3/en

Links

Classifications

    • 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
    • C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D277/12—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D277/18—Nitrogen atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/10—Anthelmintics
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C335/04—Derivatives of thiourea
    • C07C335/16—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C335/20—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups

Claims (2)

кислоты с обратным холодильником. После упаривани  и кристаллизации остатка смеси из этаиола и-воды получают 18,8 г хлоргиДрата 2- (4-аминофенилимий.о) -N-метилтиазолидина с т. пл.270°С, из которого после добавлени  натриевой щелочи получают свободное основание с т. пл. 130-131°С (полученное повторной кристаллизацией из уксусното эфира). Выход 77,5% от теории. Пример 2. Описанным в примере I методом получают производные тиазолидина формулы I со следующими значени ми R и R. т. пл., С НС1 194 (разложение) СНз 104-105 2HCI 245 CHj-СН СН2 Формула изобретени  Способ получени  2- (л-аминофенилимино) З-аза-1-тиациклоалканов или их солей общей формулы - :(СН,)ЛТ где R -алкил, содержащий 1-3 атома углерода , аллил; R - водород, галоид; п - целое число 2 или 3; или их солей, отличающийс  тем, что соединение общей формулы X.jj(CH2)n Д где R, R, п имеют вышеуказанные значени ; R - алкоксил, содержащий 1-3 атома углерода, фурил, водород, фенил, незамещеиный или моно- или дизамещенный галогеном, ал килом с числом атомов углерода 1-3, алкоксилом с числом атомов углерода 1-3 или нитрогруппой, алкил, незамещенный или замещенный алкоксигруппой с числом атомов углерода 1-3 или феноксигруппой, подвергают гидролизу разбавленной сол ной или серной кислотой в водной среде или в среде водорастворимого спирта, или концентрированной сол ной кислотой, с последующим выделением продуктов в свободном виде или в виде соли. acid reflux. After evaporation and crystallization of the remainder of the mixture from ethanol and water, 18.8 g of chlorohydrate 2- (4-aminophenylimium.o) -N-methylthiazolidine with mp. 270 ° C are obtained, from which, after adding sodium alkali, the free base is obtained pl. 130-131 ° C (obtained by recrystallization from ethyl acetate). Output 77.5% of theory. Example 2. The method described in Example I was used to prepare thiazolidine derivatives of the formula I with the following values of R and R. M. pl. C HC1 194 (decomposition) CH 3 104-105 2HCI 245 CHj-CH 2 CH 2 The formula of the invention Preparation method 2- (L -aminophenylimino) 3-aza-1-thiacycloalkanes or their salts of the general formula -: (CH,) LT where R is alkyl containing 1 to 3 carbon atoms, allyl; R is hydrogen, halogen; n is an integer of 2 or 3; or their salts, characterized in that the compound of the general formula X.jj (CH2) n D, where R, R, n have the above values; R is alkoxy containing 1-3 carbon atoms, furyl, hydrogen, phenyl, unsubstituted or mono- or disubstituted with halogen, alkyl with 1-3 carbon atoms, alkoxyl with 1-3 carbon atoms or nitro, alkyl, unsubstituted or substituted by an alkoxy group with 1-3 carbon atoms or a phenoxy group, is hydrolyzed with dilute hydrochloric or sulfuric acid in an aqueous medium or in a water-soluble alcohol medium, or concentrated hydrochloric acid, followed by isolation of the products in free form or as a salt. 2. Способ по п. 1, отличающийс  тем, что процесс ведут при температуре кипени  растворител . Источник информации, прин тый во внимание при экспертизе 1. Е. Cherbuliez, В. Willhalm, S. Jahard. . Rabinowitz. «Recherches sur la farmation et e transformation des esters, LXXVHI. Helv. hem. Acta., 50, 2563, 1967.2. A method according to claim 1, characterized in that the process is carried out at the boiling point of the solvent. The source of information taken into account during the examination 1. E. Cherbuliez, V. Willhalm, S. Jahard. . Rabinowitz. “Recherches sur la farmation et al transformation des esters, LXXVHI. Helv. hem. Acta., 50, 2563, 1967.
SU1827228A 1971-09-14 1972-09-12 The method of obtaining 2- (α-aminophenylimino) -3-aza-1-thiacycloalkanes or their salts SU556728A3 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE2145807A DE2145807A1 (en) 1971-09-14 1971-09-14 2- (AMINOPHENYLIMINO) -3-AZA-1-THIACYCLOALKANE, METHOD OF MANUFACTURING AND USE AS A MEDICINAL PRODUCT

Publications (1)

Publication Number Publication Date
SU556728A3 true SU556728A3 (en) 1977-04-30

Family

ID=5819465

Family Applications (4)

Application Number Title Priority Date Filing Date
SU1827231A SU455544A3 (en) 1971-09-14 1972-09-12 Method for preparing 2- (aminophenylolimino) 3-aza-1-thiacycloalkanes
SU1827230A SU439988A3 (en) 1971-09-14 1972-09-12 The method of obtaining 2- (aminophenylimino) -3az-1-tiacycloalkanes
SU1827229A SU505363A3 (en) 1971-09-14 1972-09-12 Method for preparing 2- (aminophenylimino) -3-aza-1-thiacycloalkanes
SU1827228A SU556728A3 (en) 1971-09-14 1972-09-12 The method of obtaining 2- (α-aminophenylimino) -3-aza-1-thiacycloalkanes or their salts

Family Applications Before (3)

Application Number Title Priority Date Filing Date
SU1827231A SU455544A3 (en) 1971-09-14 1972-09-12 Method for preparing 2- (aminophenylolimino) 3-aza-1-thiacycloalkanes
SU1827230A SU439988A3 (en) 1971-09-14 1972-09-12 The method of obtaining 2- (aminophenylimino) -3az-1-tiacycloalkanes
SU1827229A SU505363A3 (en) 1971-09-14 1972-09-12 Method for preparing 2- (aminophenylimino) -3-aza-1-thiacycloalkanes

Country Status (22)

Country Link
US (1) US3860590A (en)
JP (2) JPS4836168A (en)
AT (1) AT322548B (en)
AU (1) AU464649B2 (en)
BE (1) BE788743A (en)
CA (1) CA1007638A (en)
CH (2) CH569724A5 (en)
DD (2) DD103898A5 (en)
DE (1) DE2145807A1 (en)
EG (1) EG11037A (en)
ES (4) ES406622A1 (en)
FR (1) FR2154512B1 (en)
GB (1) GB1377265A (en)
HU (1) HU167410B (en)
IE (1) IE36698B1 (en)
IL (1) IL40338A (en)
NL (1) NL7212419A (en)
PL (4) PL93588B1 (en)
RO (4) RO84247B (en)
SE (1) SE412756B (en)
SU (4) SU455544A3 (en)
ZA (1) ZA726271B (en)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
HU167761B (en) * 1973-07-12 1975-12-25
US4140784A (en) * 1976-09-17 1979-02-20 Ciba-Geigy Corporation Novel thiazolidines
US4163791A (en) * 1976-09-17 1979-08-07 Ciba-Geigy Corporation 2-Phenyliminothiazoline compounds
DE2758005A1 (en) 1977-12-24 1979-06-28 Bayer Ag PHOSPHONYLUREIDOBENZOL DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS MEDICINAL PRODUCTS
DE3632042A1 (en) * 1986-03-08 1987-09-10 Bayer Ag DIARYLSULFID DERIVATIVES
US6353006B1 (en) 1999-01-14 2002-03-05 Bayer Corporation Substituted 2-arylimino heterocycles and compositions containing them, for use as progesterone receptor binding agents
CN1247553C (en) 1999-09-14 2006-03-29 盐野义制药株式会社 2-imino-1,3-thiazine derivs.
DE102008030764A1 (en) * 2008-06-28 2009-12-31 Bayer Animal Health Gmbh Combination of amidine derivatives with cyclic depsipeptides

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US327708A (en) * 1885-10-06 Wet-ore concentrator
US2877232A (en) * 1957-12-31 1959-03-10 Ciba Pharm Prod Inc 2-(4-isopentyloxyphenyl)-imino, 3 (4-isopentyloxyphenyl)-thiazolidine and therapeutically useful salts
US3297708A (en) * 1965-10-06 1967-01-10 American Cyanamid Co Method of preparing thiazolidines
FR1516854A (en) * 1966-12-20 1968-02-05 Aquitaine Petrole Process for the production of imino-thiazolidines

Also Published As

Publication number Publication date
AU4660472A (en) 1974-03-21
IE36698B1 (en) 1977-02-02
RO68372A (en) 1981-06-26
ES406622A1 (en) 1976-01-16
RO84247A (en) 1984-05-23
PL89701B1 (en) 1976-12-31
RO84247B (en) 1984-07-30
JPS4836169A (en) 1973-05-28
SE412756B (en) 1980-03-17
AU464649B2 (en) 1975-09-04
PL93588B1 (en) 1977-06-30
NL7212419A (en) 1973-03-16
JPS4836168A (en) 1973-05-28
ES436202A1 (en) 1977-02-16
GB1377265A (en) 1974-12-11
IL40338A0 (en) 1972-11-28
DD105990A5 (en) 1974-05-20
IE36698L (en) 1973-03-14
HU167410B (en) 1976-04-28
US3860590A (en) 1975-01-14
CH587258A5 (en) 1977-04-29
RO84248B (en) 1984-07-30
SU439988A3 (en) 1974-08-15
BE788743A (en) 1973-03-13
RO68389A (en) 1981-09-24
ZA726271B (en) 1973-06-27
DE2145807A1 (en) 1973-03-22
ES436200A1 (en) 1977-01-16
CH569724A5 (en) 1975-11-28
SU505363A3 (en) 1976-02-28
IL40338A (en) 1976-01-30
CA1007638A (en) 1977-03-29
FR2154512A1 (en) 1973-05-11
RO84248A (en) 1984-05-23
PL93690B1 (en) 1977-06-30
PL93669B1 (en) 1977-06-30
DD103898A5 (en) 1974-02-12
AT322548B (en) 1975-05-26
FR2154512B1 (en) 1976-04-23
SU455544A3 (en) 1974-12-30
ES436201A1 (en) 1977-01-16
EG11037A (en) 1977-12-31

Similar Documents

Publication Publication Date Title
GB1209946A (en) Homopyrimidazole derivatives
GB1305793A (en)
US3409669A (en) 2-(cyclohexylamino)-2-methyl-propylguanidine-1 and the salts and hydrate thereof
SU556728A3 (en) The method of obtaining 2- (α-aminophenylimino) -3-aza-1-thiacycloalkanes or their salts
US2483436A (en) Thioethers and methods for obtaining the same
GB1091394A (en) Novel process for the preparation of unsaturated cyclic ketones
ES320729A1 (en) Procedure for the synthesis of new derivatives of antranilic acid. (Machine-translation by Google Translate, not legally binding)
GB1029221A (en) Triarylalkane derivatives
ES446691A1 (en) Biphenyl derivatives and pharmaceutical compositions thereof
SU569287A3 (en) Method of preparation of benzhydryloxyalkylamine derivatives or salts thereof
ES405650A1 (en) Procedure for the preparation of new acids 4- (4 bifenilil) -4-hydroxy-butirrics, its esteres or lactonas. (Machine-translation by Google Translate, not legally binding)
SU390091A1 (en) METHOD OF OBTAINING 1-ARENSULPHONYL-4-aryl-dehydroquinoxalines
ES406367A1 (en) Thiazolino-pyrimidin-5-one derivatives, process for their preparation and applications thereof
GB1085066A (en) Substituted alkylpiperidines and methods of preparation thereof
SU64449A1 (en) The method of producing tertiary amines of the type, R2NCH2R1
Carson Jr et al. Xylitol esters of fatty acids
SU99299A1 (en) The method of alkylation of 3,5-dicarbmeto-xianiline with octadecylbromide
ES396174A1 (en) Phenylethanolamine derivatives
US2806858A (en) New anticoagulants
SU481593A1 (en) The method of obtaining derivatives of 1,2-diazetin 1,2-dioxides
SU362022A1 (en) METHOD FOR OBTAINING PHOSPHOLYLATED THIOSEMICARBAZONES
GB667199A (en) Process for stabilizing photographic emulsions
GB1022960A (en) Basic alcohol esters of heterocyclic acids, compositions thereof, and method of making and using
GB1001827A (en) Araliphatic amines, a process for their manufacture and pharmaceutical preparations containing them
GR27795B (en) METHOD FOR THE PREPARATION OF NEW HETEROCYCLIC COMPOUNDS.