DK145227B - Analogifremgangsmaade til fremstilling af 4',5-dinitro-3'-trifluormethyl-2-thiophencarboxylsyreanilid - Google Patents
Analogifremgangsmaade til fremstilling af 4',5-dinitro-3'-trifluormethyl-2-thiophencarboxylsyreanilid Download PDFInfo
- Publication number
- DK145227B DK145227B DK465772AA DK465772A DK145227B DK 145227 B DK145227 B DK 145227B DK 465772A A DK465772A A DK 465772AA DK 465772 A DK465772 A DK 465772A DK 145227 B DK145227 B DK 145227B
- Authority
- DK
- Denmark
- Prior art keywords
- dinitro
- preparation
- formula
- ananilide
- thiophencarboxylic
- Prior art date
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Classifications
-
- 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
- C07D333/26—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 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
- C07D333/42—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 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 with nitro or nitroso radicals directly attached to ring carbon atoms
- C07D333/44—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 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 with nitro or nitroso radicals directly attached to ring carbon atoms attached in position 5
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D307/70—Nitro radicals
- C07D307/71—Nitro radicals attached in position 5
- C07D307/72—Nitro radicals attached in position 5 with hydrocarbon radicals, substituted by nitrogen-containing radicals, attached in position 2
- C07D307/73—Nitro radicals attached in position 5 with hydrocarbon radicals, substituted by nitrogen-containing radicals, attached in position 2 by amino or imino, or substituted amino or imino radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (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 Compounds Containing Sulfur Atoms (AREA)
- Furan Compounds (AREA)
Description
145227
Den foreliggende opfindelse angår en analogifremgangsmåde til fremstilling af den hidtil ukendte forbindelse 4',5-dinitro-3'-trifluormethyl-2-thiophencarboxylsyreanilid med formlen no2 r"ir II) (i) kH-c°^ JLN°2 s 5 Fremgangsmåden ifølge opfindelsen er ejendommelig ved, at man i et opløsningsmiddel ved en temperatur på 20°C eller mere omsætter omtrent ækvimolekulære mængder af anilinen med formlen: N02 CFo (II) L2 10 og syrechloridet med formlen: Ϊ li (III) ci-co—y— no2
Anvendelige opløsningsmidler er de, der kan anvendes til udførelse af reaktionen mellem et syrechlorid og en amin.
Man kan især som egnede opløsningsmidler nævne tetrahydro= 15 furan, pyridin, dimethylformamid, aromatiske hydrocarboner såsom benzen, toluen, xylen,chlorerede hydrocarboner såsom chloroform, samt blandinger af disse opløsningsmidler. Foretrukne opløsningsmidler ved fremgangsmåden ifølge opfindelsen er benzen og pyridin, idet pyridin anvendes under de 20 specielle betingelser, der beskrives nedenfor.
145227 2
Fortrinsvis sætter man under omrøring en støkiometrisk mængde syrechlørid III til en opløsning af 100-200 g pr. liter af anilinen II i pyridin, holder reaktionsblandingen på en temperatur lig med eller over 20°C og udfælder den således dan-5 nede forbindelse med foralen I med IN saltsyre. Pyridin har den fordel, at den forener sig med HC1 dannet under reaktionen og giver pyridinhydrochlorid, som er opløseligt i vand.
Forbindelsen franstillet ifølge opfindelsen er anvendelig i terapien, især som antibakterielt middel. Forbindelsen er også virk-10 som overfor svampe og parasitter.
Opfindelsen illustreres nærmere af følgende eksempel.
Eksempel 45-dinitro-3 ' -trif luoraethyl-2-thiophencarboxylsyreanilid, kode nr. Rd 1087.
F3 _ 15 02N—— NH-CO—NQ2
Til en opløsning af 3,5 g 4-nitro-3-trifluormethylanilin i 20 ml tør pyridin sættes hurtigt under omrøring 3,2 g 2-(5-nitro= thiophen)-carboxylsyrechlorid. Der sker en spontan temperaturstigning til en værdi over 20°C. Man kan afvente nogle minut-20 ter, og derefter hældes opløsningen i et tilstrækkeligt rumfang IN saltsyre, og man afkøler. Derefter omkrystalliseres af ethanol ved -15°C. Der fremkom 3,5 g 4',5-dinitro-3*-trifluor= methyl-2-thiophencarboxylsyreanilid (udbytte 58%), smp. 164°C.
Ved oral administration til mus udviser forbindelsen fremstil-25 let ifølge opfindelsen en mindste lethal dosis, som er større end 3 mg/kg.
145227 3
Forbindelsen udviser bedre antibakterielle egenskaber end beslægtede kendte forbindelser, således som det fremgår af nedenstående sammenligningsforsøg. Sammenligningsforbindelsen A er forbindelse 1 i artiklen J. Med. Chera. 10 (1967), 5 side 93-95, med formlen |°2 |rCP3 !JH-C0-CH3
Sammenligningsforbindelsen B er forbindelse 25 i artiklen J. Med. Chem. 12 (1969), side 957-9, med formlen N02 /γ®3 rø-CO —N02 10 Den antibakterielle virkning blev bestemt på følgende måde: Forbindelser, der skal undersøges, opløses i acetone. Man fremstiller en række opløsninger med aftagende koncentration (fra 1000 ug/ml) ved hjælp af næringsbouillon. Opløs- 5 ningerne podes med ca. 10 bakterier (stafylokokker) pr.
15 ml ved anvendelse af en podekultur fremkommet ved dyrkning i 24 timer i næringsbouillon. Prøverne studeres hvert døgn under en uges inkubering ved 37°C. Den mindst hæmmende koncentration defineres som koncentrationen af den sidste opløsning, hvori der ikke sker nogen bakterieudvikling ved 20 afslutning af iagttagelsestiden.
Claims (2)
145227 Resultater Forbindelse Mindste hæmmende kone, ug/ml Fremstillet ifølge opfindelsen ® ^ A «1000
5 B >1000 Fatentkrav Analogifremgangsmåde til fremstilling af 4',5-dinitro-3'-trifluormethyl-2-thiophencarboxylsyreanilid, der har formlen P°2 jJ~CF3 (I) NH-CO —— NO 2 kendetegnet ved, at man i et opløsningsmiddel 10 ved en temperatur på 20°C eller mere omsætter omtrent ækvi-molekulære mængder af anilinen med formlen [°2 CF3 (II) X og syrechloridet med formlen C1-C0—- N02 (III)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4423971A GB1401975A (en) | 1971-09-22 | 1971-09-22 | 3-trifluoromethyl-anilides |
| GB4423971 | 1971-09-22 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DK145227B true DK145227B (da) | 1982-10-11 |
| DK145227C DK145227C (da) | 1983-03-07 |
Family
ID=10432404
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK465772A DK145227C (da) | 1971-09-22 | 1972-09-21 | Analogifremgangsmaade til fremstilling af 4',5-dinitro-3'-trifluormethyl-2-thiophencarboxylsyreanilid |
Country Status (16)
| Country | Link |
|---|---|
| JP (1) | JPS4839450A (da) |
| AU (1) | AU474208B2 (da) |
| BE (1) | BE788983A (da) |
| CH (1) | CH560181A5 (da) |
| DK (1) | DK145227C (da) |
| ES (1) | ES406911A1 (da) |
| FR (1) | FR2154499B1 (da) |
| GB (1) | GB1401975A (da) |
| IL (1) | IL40398A (da) |
| LU (1) | LU66118A1 (da) |
| NL (1) | NL155829B (da) |
| NO (1) | NO137940C (da) |
| OA (1) | OA04181A (da) |
| RO (1) | RO67638A (da) |
| SE (1) | SE395695B (da) |
| ZA (1) | ZA726425B (da) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1252041A (en) * | 1983-09-28 | 1989-04-04 | Kamlesh Gaglani | Industrial fungicides |
| US8445687B2 (en) * | 2007-09-10 | 2013-05-21 | Cipla Limited | Process for the preparation of a RAF kinase inhibitor and intermediates for use in the process |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1593586A (da) * | 1967-10-17 | 1970-06-01 |
-
0
- BE BE788983D patent/BE788983A/xx not_active IP Right Cessation
-
1971
- 1971-09-22 GB GB4423971A patent/GB1401975A/en not_active Expired
-
1972
- 1972-09-12 FR FR7232293A patent/FR2154499B1/fr not_active Expired
- 1972-09-14 CH CH1348172A patent/CH560181A5/xx not_active IP Right Cessation
- 1972-09-20 IL IL40398A patent/IL40398A/xx unknown
- 1972-09-20 ZA ZA726425A patent/ZA726425B/xx unknown
- 1972-09-20 LU LU66118A patent/LU66118A1/xx unknown
- 1972-09-21 NO NO3382/72A patent/NO137940C/no unknown
- 1972-09-21 NL NL7212788.A patent/NL155829B/xx not_active IP Right Cessation
- 1972-09-21 SE SE7212194A patent/SE395695B/xx unknown
- 1972-09-21 AU AU46921/72A patent/AU474208B2/en not_active Expired
- 1972-09-21 RO RO7272296A patent/RO67638A/ro unknown
- 1972-09-21 DK DK465772A patent/DK145227C/da not_active IP Right Cessation
- 1972-09-21 ES ES406911A patent/ES406911A1/es not_active Expired
- 1972-09-22 OA OA54695A patent/OA04181A/xx unknown
- 1972-09-22 JP JP47095656A patent/JPS4839450A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| SE395695B (sv) | 1977-08-22 |
| NL155829B (nl) | 1978-02-15 |
| FR2154499A1 (da) | 1973-05-11 |
| DK145227C (da) | 1983-03-07 |
| IL40398A0 (en) | 1972-11-28 |
| DE2246308B2 (de) | 1977-02-17 |
| BE788983A (fr) | 1973-01-15 |
| RO67638A (ro) | 1982-04-12 |
| ZA726425B (en) | 1973-06-27 |
| CH560181A5 (da) | 1975-03-27 |
| GB1401975A (en) | 1975-08-06 |
| JPS4839450A (da) | 1973-06-09 |
| IL40398A (en) | 1975-07-28 |
| NO137940B (no) | 1978-02-13 |
| NL7212788A (da) | 1973-03-26 |
| AU4692172A (en) | 1974-03-28 |
| OA04181A (fr) | 1979-12-31 |
| ES406911A1 (es) | 1975-09-16 |
| FR2154499B1 (da) | 1975-11-28 |
| NO137940C (no) | 1978-05-24 |
| AU474208B2 (en) | 1976-07-15 |
| DE2246308A1 (de) | 1973-03-29 |
| LU66118A1 (da) | 1973-01-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PBP | Patent lapsed |