PL130008B2 - Process for preparing novel 2-phenyl-4-/3'-trifluoromethyl-4'-chlorophenylamino/-6-methylpyrimidin-5-carboxylic acid - Google Patents
Process for preparing novel 2-phenyl-4-/3'-trifluoromethyl-4'-chlorophenylamino/-6-methylpyrimidin-5-carboxylic acid Download PDFInfo
- Publication number
- PL130008B2 PL130008B2 PL23861082A PL23861082A PL130008B2 PL 130008 B2 PL130008 B2 PL 130008B2 PL 23861082 A PL23861082 A PL 23861082A PL 23861082 A PL23861082 A PL 23861082A PL 130008 B2 PL130008 B2 PL 130008B2
- Authority
- PL
- Poland
- Prior art keywords
- phenyl
- carboxylic acid
- trifluoromethyl
- chlorophenylamino
- methylpyrimidin
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 claims description 4
- MGRYVXAAUYHOSI-UHFFFAOYSA-N 4-methylpyrimidine-5-carboxylic acid Chemical compound CC1=NC=NC=C1C(O)=O MGRYVXAAUYHOSI-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ASPDJZINBYYZRU-UHFFFAOYSA-N 5-amino-2-chlorobenzotrifluoride Chemical compound NC1=CC=C(Cl)C(C(F)(F)F)=C1 ASPDJZINBYYZRU-UHFFFAOYSA-N 0.000 description 2
- PXYZOZYWEWVPHO-UHFFFAOYSA-N OC(=O)C=1C(C)=NC(C=2C=CC=CC=2)=NC=1NC1=CC=C(Cl)C(C(F)(F)F)=C1 Chemical compound OC(=O)C=1C(C)=NC(C=2C=CC=CC=2)=NC=1NC1=CC=C(Cl)C(C(F)(F)F)=C1 PXYZOZYWEWVPHO-UHFFFAOYSA-N 0.000 description 2
- 230000003385 bacteriostatic effect Effects 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 1
- KGWNRZLPXLBMPS-UHFFFAOYSA-N 2h-1,3-oxazine Chemical compound C1OC=CC=N1 KGWNRZLPXLBMPS-UHFFFAOYSA-N 0.000 description 1
- 241000186031 Corynebacteriaceae Species 0.000 description 1
- 241000192125 Firmicutes Species 0.000 description 1
- 241000295644 Staphylococcaceae Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- PLHJDBGFXBMTGZ-WEVVVXLNSA-N furazolidone Chemical compound O1C([N+](=O)[O-])=CC=C1\C=N\N1C(=O)OCC1 PLHJDBGFXBMTGZ-WEVVVXLNSA-N 0.000 description 1
- 229960001625 furazolidone Drugs 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- NXFQHRVNIOXGAQ-YCRREMRBSA-N nitrofurantoin Chemical compound O1C([N+](=O)[O-])=CC=C1\C=N\N1C(=O)NC(=O)C1 NXFQHRVNIOXGAQ-YCRREMRBSA-N 0.000 description 1
- 229960000564 nitrofurantoin Drugs 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- JNMRHUJNCSQMMB-UHFFFAOYSA-N sulfathiazole Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CS1 JNMRHUJNCSQMMB-UHFFFAOYSA-N 0.000 description 1
- 229960001544 sulfathiazole Drugs 0.000 description 1
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- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Przedmiotem wynalazku jest sposób wytwarzania nowego kwasu 2-fenylo-4-(3'-trifluoro- metylo-4'-chlorofenyloamino)-6-metylopirymidyno-5-karboksylowego o wzorze 1. Zwiazek wyt¬ worzony sposobem wedlug wynalazku stanowi produkt wyjsciowy do wytworzenia jego nowej pochodnej o wzorze 2, która w badaniach biologicznych wykazuje wlasciwosci przeciwbakteryjne.Wedlug wynalazku sposób wytwarzania nowego kwasu 2-fenylo-4-(3'-trifluorometylo-4'- chlorofenyloamino)-6-metylopirymidyno-5-karboksylowego o wzorze 1 polega na tym, ze kwas 2-fenylo-4~tio-6-metylopirymidyno-5-karboksylowy stapia sie z 3-trifluorometylo-4-chloroanilina w temperaturze 180-200°C.Nieoczekiwanie okazalo sie, ze przeprowadzenie kwasu 2-fenylo-4-tio-6-metylopirymidyno-5- karboksylowego w wymieniony aminokwas, pochodny pierscienia pirymidynowego, pozwala na wytworzenie zwiazku, który nastepnie poddany cyklizacji w temperaturze pokojowej dzialaniem chloromrówczanu etylu prowadzi do wytworzenia nowego l-(3'-trifluorometylo-4'-chlorofenylo) (2,4H)-5-metylo-7-fenylopirymidyno[4,5-d][l,3] oksazyno 2,4-dionu o wzorze 2, wykazujacego dzialanie przeciwbakteryjne w stosunku do bakterii Gram dodatnich, czego nie mozna bylo zgóry przewidziec. Dzialanie bakteriostatyczne otrzymanego dionu zostalo potwierdzone w testach przeciwbakteryjnych na podstawie hamowania rozrostu licznych szczepów drobnoustrojów w warunkach in vitro, w których zwiazek ten wykazuje aktywnosc silnie hamujaca w stosunku do gronkowców, paciorkowców i maczugowców w stezeniach 50-30 jug/ml pozywki. Dzialanie bakte¬ riostatyczne przewyzsza dzialanie sulfatiazolu, furazolidonu, nitrofurantoiny i trimetaprimu w analogicznych stezeniach, wynoszacych 1-lOjLtg/ml.Przedmiot wynalazku jest przedstawiony w przykladzie wykonania.Przyklad. 5g kwasu2-fenylo-4-tio-6-metylopirymidyno-5-karboksylowego stapia sie z4g 3-trifluorometylo-4-chloroaniliny w temperaturze 190°C przez czas 5 godzin. Nastepnie calosc krystalizuje sie z metanolu. Otrzymuje sie 3,8 g produktu z wydajnoscia równa 58% wydajnosci teoretycznej. Zwiazek ma postac bialych krysztalów o temperaturze topnienia 212-214°C.2 130008 Zastrzezenie patentowe Sposób wytwarzania nowego kwasu 2-fenylo-4-(3/-trifluorometylo-4'-chIorofenyloamino)-6- metylopirymidyno-5-karboksylowego o wzorze 1, znamienny tym, ze kwas 2-fenylo-4-tio-6- metylopirymidyno-5-karboksylowy stapia sie z 3-trifluoromety!o-4-chloroanilina w temperaturze 180-200°C.Pracownia Poligraficzna UP PRL. Naklad 100 egz.Cena 100 zl PL
Claims (1)
1. Zastrzezenie patentowe Sposób wytwarzania nowego kwasu 2-fenylo-4-(3/-trifluorometylo-4'-chIorofenyloamino)-6- metylopirymidyno-5-karboksylowego o wzorze 1, znamienny tym, ze kwas 2-fenylo-4-tio-6- metylopirymidyno-5-karboksylowy stapia sie z 3-trifluoromety!o-4-chloroanilina w temperaturze 180-200°C. Pracownia Poligraficzna UP PRL. Naklad 100 egz. Cena 100 zl PL
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL23861082A PL130008B2 (en) | 1982-10-11 | 1982-10-11 | Process for preparing novel 2-phenyl-4-/3'-trifluoromethyl-4'-chlorophenylamino/-6-methylpyrimidin-5-carboxylic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL23861082A PL130008B2 (en) | 1982-10-11 | 1982-10-11 | Process for preparing novel 2-phenyl-4-/3'-trifluoromethyl-4'-chlorophenylamino/-6-methylpyrimidin-5-carboxylic acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL238610A2 PL238610A2 (en) | 1983-08-15 |
| PL130008B2 true PL130008B2 (en) | 1984-06-30 |
Family
ID=20014317
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL23861082A PL130008B2 (en) | 1982-10-11 | 1982-10-11 | Process for preparing novel 2-phenyl-4-/3'-trifluoromethyl-4'-chlorophenylamino/-6-methylpyrimidin-5-carboxylic acid |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL130008B2 (pl) |
-
1982
- 1982-10-11 PL PL23861082A patent/PL130008B2/pl unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL238610A2 (en) | 1983-08-15 |
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