DE1959117A1 - New organic compounds and processes for their production - Google Patents
New organic compounds and processes for their productionInfo
- Publication number
- DE1959117A1 DE1959117A1 DE19691959117 DE1959117A DE1959117A1 DE 1959117 A1 DE1959117 A1 DE 1959117A1 DE 19691959117 DE19691959117 DE 19691959117 DE 1959117 A DE1959117 A DE 1959117A DE 1959117 A1 DE1959117 A1 DE 1959117A1
- Authority
- DE
- Germany
- Prior art keywords
- salts
- ethyl
- compounds
- methyl
- subsequently converted
- Prior art date
- Legal status (The legal status 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 status listed.)
- Pending
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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cephalosporin Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Description
SandOZ AO. Patonfanwäf«SandOZ AO. Patonfanwäf "
Dr.W.Schc!k,D;p!.-lng.P.Wirrfi _Dr.W.Schc! K, D; p! .- lng.P.Wirrfi _
Dipl,ln3.G.Dcnner,berg Case 600-6249 Dipl, ln 3 .G.Dnner, Berg Case 600-6249
Dr. V. SclimiecJ-'CowarEik
Dr. P. Weinhold, Dr. D. Gudel
6 Frankfurt/M., Gr. Eschenheimer Sir. 39 Dr. V. SclimiecJ-'CowarEik
Dr. P. Weinhold, Dr. D. Gudel
6 Frankfurt / M., Gr. Eschenheimer sir. 39
Neue New organische Verbindungen und organic compounds and Verfahren procedure zu ihrerto their
Die vorliegende Erfindung betrifft Verbindungen der allg. Formel I, worin Jedes R unabhängig voneinander für eine Alkylgruppe mit 1-4 Kohlenstoffatomen, R, für Wasserstoff oder eine geradekettlge Alkylgruppe mit 1-3 Kohlenstoffatomen und Jedes X unabhängig voneinander für Wasserstoff, Fluor oder Chlor stehen, wobei Jedooh zumindest ein X Chlor oder Fluor bedeutet und ihre Säureadditionssalze sowie Verfahren zur Herstellung von Verbindungen der allg. Formel I und ihrer Säureadditionssalze,The present invention relates to compounds of the general formula I in which each R is independently an alkyl group with 1-4 carbon atoms, R is hydrogen or a straight-chain alkyl group with 1-3 carbon atoms and each X is independently hydrogen, fluorine or chlorine , wherein Jedooh at least one X is chlorine or fluorine and their acid addition salts and processes for the preparation of compounds of the general formula I and their acid addition salts,
In den erfindungsgemässen Verbindungen der allg. Formel I steht R, das eine Alkylgruppe mit 1-4 Kohlenstoffatomen bedeutet, insbesondere für Methyl, Aethyl oder Isopropyl, R,, falls es eine geradekettige Alkylgruppe mit 1-5 Kohlenstoffatomen bedeutet, insbesondere für Methyl, Aethyl und Propyl. Bevorzugte Verbindungen der allg. Formel I besitzen im Phenylring einen p-Chlorosubstituenten. .In the compounds of the general formula I according to the invention R represents an alkyl group having 1-4 carbon atoms, in particular methyl, ethyl or isopropyl, R ,, if it is a straight chain alkyl group of 1-5 carbon atoms means, in particular for methyl, ethyl and propyl. Preferred Compounds of general formula I have a phenyl ring a p-chloro substituent. .
ErfIndungsgemäss kann man zu Verbindungen der allg· Formel I und ihren Säureadditionssalzen gelangen, indem man Verbindungen der allg. Formel II, worin R1 und X obige Bedeutung besitzen und X1 für Chlor oder Brom steht, mit Verbindungen der allg.According to the invention, compounds of the general formula I and their acid addition salts can be obtained by mixing compounds of the general formula II, in which R 1 and X have the above meanings and X 1 is chlorine or bromine, with compounds of the general formula II.
008824/2017008824/2017
BAD ORlGlNAtBAD ORlGlNAt
600-6249600-6249
Fo»©l IHj, E7®2?ia 1 ©feige Beet©ufeii»g besitz in einem watew ά®η B<§akfe£@&{§te©di!sgungea inerten ©rgantsotaa Lösungsmittel bei Temperaturen zwischen 0° und βθθ C umsetzt und die sq erhalfeenea Usplbinduagen äer allg» Formel X gegebenenfalls in ihre Säureaddifeionssalze überführt.·Fo »© l IHj, E7®2? Ia 1 © fig bed © ufeii» g owned in a watew ά®η B <§akfe £ @ & {§te © di! Sgungea inert © rgantsotaa solvents at temperatures between 0 ° and βθ θ C and converts the sq erhalfeenea Usplbinduagen äer general formula X, if necessary, into their acid addition salts.
Die erfindungsgemässe Umsetzung kann beispielsweise unter Verwendung von Aceton, Tetrahydrofuran oder niederen Alkoholen, wie Aethanol, als unter den Heaktionebedlngungen inerte organische Lösungsmittel durchgeführt werden, wobei die Reaktionstemperatur zwischen 0° und 60° C, vorzugsweise zwischen 1ΘΘ und 35° C betragen soll. Die verwendeten Lösungsmittel goi-ji© Temperaturen sind jedoch nicht' kritisch* Die Umsetzung kann zwar in Gegenwart eines säurebindenden Mittels»The inventive reaction may for example using acetone, tetrahydrofuran or lower alcohols, such as ethanol, are used as carried out under the Heaktionebedlngungen inert organic solvent, wherein the reaction temperature is between 0 ° and 60 ° C, preferably should be between 1Θ Θ and 35 ° C. However, the goi-ji © solvents used are not 'critical * The reaction can take place in the presence of an acid-binding agent »
NatriumbiGarbonat oder
beispielsweise/eines Ueberschusses an Verbindungen der allg·
Formel III erfolgen* es ist jedoch vorteilhafter, die Umsetzung go durchzuführen^ dass Säureadditionssalze von
Verbindungen der allg. Formel I gebildet werden.Sodium bicarbonate or
for example / an excess of compounds of the general formula III * it is more advantageous to carry out the reaction ^ that acid addition salts of compounds of the general formula I are formed.
Di© ¥©Aiiiäimg@a der allge- Formel I weröen zweelonässigerwelse in Form ilii3©^ Sämi*esdditionssalge isolierto Aus ihren Säur©" additionssülgen köimea die freien Basen beispielsweise durch Beteidlurag mi% wässrigen Natrium@&r&osi&t-L@sung@n freigesetztDi © ¥ © Aiiiäimg @ a of the general e - weröen formula I zweelonässigerwelse in the form ilii 3 © ^ Sämi * esdditionssalge isolated o From their Saur © "additionssülgen köimea the free bases, for example, by Beteidlurag mi% aqueous sodium @ & r & osi t-L @ solution @ n released
Di® ©fffDi® © fff
ailge Formel I köailg e formula I kö
la tamtomeroK1 Form auftreten«, Diese tautomere For® ü fliiF@h di© allgo Formel TWΰ worin Rr, K1 'und Ii obige 'la tamtomeroK 1 form occur «, This tautomeric For® ü fliiF @ h di © allgo formula TW ΰ where R r , K 1 'and Ii above'
i© f @t allg οi © f @t general ο
ά®τ· ail go ά®τ · ail go
fe dl© ©FfiMraigsgesaägg als Afe dl © © FfiMraigsgesaägg as A
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BAD ORIGINALBATH ORIGINAL
Einige der als Ausgangsverbindungen verwendeten Verbindungen der allg« Formeln II und XII sind bekannt, bisher nicht bekannte Verbindungen d$r allg. Formeln II und III können aus bekannten AusgangsverbiMungen nach bekannten Verfahren hergestellt werden. .Some of the compounds of the general formulas II and XII used as starting compounds are known, but not so far known compounds of the general formulas II and III can from known starting compounds according to known processes getting produced. .
Die erfindungsgemäss hergestellten Verbindungen der allg. Formel I sind Basen, die durch Umsetzung mit geeigneten organ!schon und anorganischen Säuren in ihre Säureadditionssalze übergeführt werdeil können. Geeignete Salze mit entsprechenden Mineralsäure sind beispielsweise die Hydrochloride, Hydrobromide, Sulfate, Phosphate und mit entsprechenden organischen Säuren die Sueeinate, Eenzeate, Acetate*, p-Toluolsulfonate etc,The compounds of the general. Formula I are bases, which by reaction with suitable bases organic and inorganic acids can be converted into their acid addition salts. Appropriate salts with appropriate Mineral acids are for example the hydrochlorides, Hydrobromides, sulfates, and phosphates with corresponding organic acids the Sueeinate, Eenzeates, Acetate *, p-Toluenesulfonate Etc,
Die Verbindungen der .allg· Formel I sowie ihre Salze besitzen ausgeprägte phanaaleodfti^jaische Eigenschaf ten und sind als Heilmittel verwendbar, Sie sselgen insbesondere eine appe ti tätige In-The compounds of the .allg · Formula I and their salts have pronounced phanaaleodfti ^ jaische properties and are used as remedies suitable, you should especially have an appe ti active in-
de Wirkung sowie eine stimulierende Wirkung auf das Zentralnervensystem
.
Die Verbindungen der allg. Formel I und ihr© SaIse können
deshalb als Appetitzügler vmü als psychische Kräftigungsmittel
verwendet wörd@rie -giaiss Erzielen des gewüsasehten therapeutischen
Erfolges sollen t&glioh 15»T5 -.ins
der allg. Formel 1, m^swgfei^is© aufgeteilt lsi
Dosen zwischen 3,8 w*ü. J3 mg 2 bis 4 mal täglieh ©der in
Retardform verabreicht,de effect as well as a stimulating effect on the central nervous system.
The compounds of the general. Formula I and their © SaIse can therefore be used as an appetite suppressant vmü as a mental tonic used woerd @ ri e -giaiss achieving gewüsasehten therapeutic success should t glioh 15 »T5 -.ins the general. Formula 1, m ^ swgfei ^ is © split lsi doses between 3.8 w * ü . J3 mg administered 2 to 4 times a day in sustained-release form,
Ueberdies besitzer* die-V-e^bin-ävngen der ailge. WötsüqI I eine entzünduiigsheminencle Mirkuisg« Die Siierftir feeraStigfc® Bosis bsträgt 150 bis 750 rag täglich,''wobei es günstig isfes diese in mehreren kleinen Dosen zwischen ^8 und 380' Γώ§0 t bis 4 mal täglich oder in Retaruform 'zu verabreichen.In addition, the owners of the ailg e . WötsüqI I a entzünduiigsheminencle Mirkuisg "The Siierftir feeraStigfc® Bosis bsträgt 150 to 750 rag per day, '' wherein s ISFE these low in several small doses of between 8 and 380 ^ '0 t Γώ§ to 4 times a day or to administer in Retaruform' .
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Fahi?o&@fav®?? iss f@P33 Fahi? O & @ fav® ?? iss f @ P33
5II = 1 5 II = 1
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Qffia©gä Mao aö IGO f' Γ 'Cg1JQffia © gä Mao aö IGO f 'Γ' Cg 1 J
üS®aiin@ai?@lgQiai©a BQäspiQlG^ Lj3l.©la© öii©üS®aiin @ ai? @ lgQiai © a BQäspiQlG ^ Lj3l. © la © öii ©
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i?pSi©ias©y2,iaE3(2;sä# iss 2@ Bi? pSi © ias © y2, iaE 3 (2; sä # iss 2 @ B
geteEisfe ■ beigeteIcefe ■ at
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!.ap^OM^pla©^!=:^^! .ap ^ OM ^ pla © ^! =: ^^
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BAD ORIGINALBATH ORIGINAL
- 7 - (SOO-6249- 7 - (SOO-6249
Alkohol SD-D*et, WasserAlcohol SD-D * et, water
50 7 in Eofc
r J 50 7 in Eofc
r J
Qmtloht unr li«^ifetel,lttn faM«tt«ß lüüsgf; iron /der Qmtloht unr li «^ ifetel, lttn faM« tt «ß lüüsgf; iron / the
M®lsg« fts Wirkstoff ab.M®lsg «fts active ingredient.
a82'4i'2O1 7a82'4i'2O1 7
BAD ORIGINALBATH ORIGINAL
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US78023668A | 1968-11-29 | 1968-11-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1959117A1 true DE1959117A1 (en) | 1970-06-11 |
Family
ID=25119019
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19691959117 Pending DE1959117A1 (en) | 1968-11-29 | 1969-11-25 | New organic compounds and processes for their production |
Country Status (8)
| Country | Link |
|---|---|
| BE (1) | BE742336A (en) |
| BR (1) | BR6914577D0 (en) |
| CH (1) | CH520702A (en) |
| DE (1) | DE1959117A1 (en) |
| ES (1) | ES373966A1 (en) |
| FR (1) | FR2024952B1 (en) |
| GB (1) | GB1289132A (en) |
| NL (1) | NL6917356A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2436263A1 (en) * | 1974-07-27 | 1976-02-12 | Hoechst Ag | THIAZOLIDE DERIVATIVES AND METHOD FOR THEIR PRODUCTION |
| DE2660158C2 (en) * | 1975-02-03 | 1985-01-24 | Frank Old Westbury N.Y. Catallo | Spreading device for spreading out and guiding knitted fabrics, in particular tubular fabrics |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB690238A (en) * | 1949-08-23 | 1953-04-15 | Knoll Ag | Process of producing 3, 4-dimethyl-5-phenyl-2-iminothiazolidine |
-
1969
- 1969-11-17 CH CH1704369A patent/CH520702A/en not_active IP Right Cessation
- 1969-11-19 NL NL6917356A patent/NL6917356A/xx unknown
- 1969-11-19 GB GB1289132D patent/GB1289132A/en not_active Expired
- 1969-11-25 DE DE19691959117 patent/DE1959117A1/en active Pending
- 1969-11-27 ES ES373966A patent/ES373966A1/en not_active Expired
- 1969-11-27 BE BE742336D patent/BE742336A/xx unknown
- 1969-11-27 BR BR21457769A patent/BR6914577D0/en unknown
- 1969-11-27 FR FR6940936A patent/FR2024952B1/fr not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2436263A1 (en) * | 1974-07-27 | 1976-02-12 | Hoechst Ag | THIAZOLIDE DERIVATIVES AND METHOD FOR THEIR PRODUCTION |
| DE2660158C2 (en) * | 1975-02-03 | 1985-01-24 | Frank Old Westbury N.Y. Catallo | Spreading device for spreading out and guiding knitted fabrics, in particular tubular fabrics |
Also Published As
| Publication number | Publication date |
|---|---|
| BE742336A (en) | 1970-05-27 |
| FR2024952A1 (en) | 1970-09-04 |
| CH520702A (en) | 1972-03-31 |
| ES373966A1 (en) | 1972-05-16 |
| NL6917356A (en) | 1970-06-02 |
| FR2024952B1 (en) | 1973-08-10 |
| GB1289132A (en) | 1972-09-13 |
| BR6914577D0 (en) | 1973-05-24 |
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