GB1374800A - Process for substitution of 1-derivatives of 1-hydroxybenzimidazoles and 1-hydroxyimidazo 4,5-b pyridines - Google Patents
Process for substitution of 1-derivatives of 1-hydroxybenzimidazoles and 1-hydroxyimidazo 4,5-b pyridinesInfo
- Publication number
- GB1374800A GB1374800A GB6011371A GB6011371A GB1374800A GB 1374800 A GB1374800 A GB 1374800A GB 6011371 A GB6011371 A GB 6011371A GB 6011371 A GB6011371 A GB 6011371A GB 1374800 A GB1374800 A GB 1374800A
- Authority
- GB
- United Kingdom
- Prior art keywords
- imidazo
- trifluoromethyl
- pyridine
- nitro
- chloro
- 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.)
- Expired
Links
- IRSPCJLMPFDMGD-UHFFFAOYSA-N 1-hydroxybenzimidazole Chemical class C1=CC=C2N(O)C=NC2=C1 IRSPCJLMPFDMGD-UHFFFAOYSA-N 0.000 title abstract 2
- 238000000034 method Methods 0.000 title 1
- 150000003222 pyridines Chemical class 0.000 title 1
- 238000006467 substitution reaction Methods 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 3
- 229910052799 carbon Inorganic materials 0.000 abstract 3
- 229910052801 chlorine Inorganic materials 0.000 abstract 3
- 229910052731 fluorine Inorganic materials 0.000 abstract 3
- 229910052736 halogen Inorganic materials 0.000 abstract 3
- 150000002367 halogens Chemical class 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 3
- 229910052717 sulfur Inorganic materials 0.000 abstract 3
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 abstract 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 150000003254 radicals Chemical class 0.000 abstract 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 abstract 1
- GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical class C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 abstract 1
- ADFFYMLJXCWABJ-UHFFFAOYSA-N 4-chloro-5,7-dinitro-2-(trifluoromethyl)-1h-benzimidazole Chemical compound [O-][N+](=O)C1=CC([N+]([O-])=O)=C2N=C(C(F)(F)F)NC2=C1Cl ADFFYMLJXCWABJ-UHFFFAOYSA-N 0.000 abstract 1
- VEXUFOBGWNNUDA-UHFFFAOYSA-N 5,6-dichloro-2-(trifluoromethyl)-1h-imidazo[4,5-b]pyridine Chemical compound ClC1=C(Cl)C=C2NC(C(F)(F)F)=NC2=N1 VEXUFOBGWNNUDA-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 abstract 1
- MPPAJXXEQAORQU-UHFFFAOYSA-N [6-chloro-2-(trifluoromethyl)imidazo[4,5-b]pyridin-1-yl] n-methylcarbamate Chemical compound C1=C(Cl)C=C2N(OC(=O)NC)C(C(F)(F)F)=NC2=N1 MPPAJXXEQAORQU-UHFFFAOYSA-N 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 abstract 1
- 229910052787 antimony Inorganic materials 0.000 abstract 1
- 229910052785 arsenic Inorganic materials 0.000 abstract 1
- 150000001556 benzimidazoles Chemical class 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 1
- 125000001589 carboacyl group Chemical group 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- RCJVRSBWZCNNQT-UHFFFAOYSA-N dichloridooxygen Chemical compound ClOCl RCJVRSBWZCNNQT-UHFFFAOYSA-N 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 150000002500 ions Chemical class 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- QLCLLKCOKMEPIR-UHFFFAOYSA-N n-(5-chloro-3-nitropyridin-2-yl)-2,2,2-trifluoroacetamide Chemical compound [O-][N+](=O)C1=CC(Cl)=CN=C1NC(=O)C(F)(F)F QLCLLKCOKMEPIR-UHFFFAOYSA-N 0.000 abstract 1
- 239000012434 nucleophilic reagent Substances 0.000 abstract 1
- -1 oxalyl halide Chemical class 0.000 abstract 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 abstract 1
- 229910052698 phosphorus Inorganic materials 0.000 abstract 1
- 238000006476 reductive cyclization reaction Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/10—Radicals substituted by halogen atoms or nitro radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10226670A | 1970-12-28 | 1970-12-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1374800A true GB1374800A (en) | 1974-11-20 |
Family
ID=22288990
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB6011371A Expired GB1374800A (en) | 1970-12-28 | 1971-12-23 | Process for substitution of 1-derivatives of 1-hydroxybenzimidazoles and 1-hydroxyimidazo 4,5-b pyridines |
| GB3830273A Expired GB1377469A (en) | 1970-12-28 | 1971-12-23 | Process for reduction of 1-derivatives of 1-hydroxy benzimidazoles and 1-hydroxyimidazo 4,5-b pyridines |
| GB3809473A Expired GB1375157A (enExample) | 1970-12-28 | 1971-12-23 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3830273A Expired GB1377469A (en) | 1970-12-28 | 1971-12-23 | Process for reduction of 1-derivatives of 1-hydroxy benzimidazoles and 1-hydroxyimidazo 4,5-b pyridines |
| GB3809473A Expired GB1375157A (enExample) | 1970-12-28 | 1971-12-23 |
Country Status (19)
| Country | Link |
|---|---|
| AR (2) | AR201728A1 (enExample) |
| AT (2) | AT312598B (enExample) |
| AU (1) | AU465099B2 (enExample) |
| BE (1) | BE777250A (enExample) |
| CA (1) | CA969547A (enExample) |
| CH (3) | CH556342A (enExample) |
| DE (2) | DE2165021A1 (enExample) |
| DK (1) | DK139385B (enExample) |
| ES (1) | ES398379A1 (enExample) |
| FR (1) | FR2121020A5 (enExample) |
| GB (3) | GB1374800A (enExample) |
| IE (1) | IE36678B1 (enExample) |
| IL (1) | IL38452A (enExample) |
| IT (1) | IT945597B (enExample) |
| NL (1) | NL7118000A (enExample) |
| SE (1) | SE412064B (enExample) |
| SU (3) | SU535905A3 (enExample) |
| YU (2) | YU35001B (enExample) |
| ZA (1) | ZA718532B (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4031107A (en) * | 1972-12-13 | 1977-06-21 | Eli Lilly And Company | Method for introducing amino groups into benzimidazole or imidazopyridine compounds |
| US4265901A (en) * | 1979-12-26 | 1981-05-05 | Eli Lilly And Company | 2-Oxybenzimidazoline compounds |
-
1971
- 1971-12-21 ZA ZA718532A patent/ZA718532B/xx unknown
- 1971-12-22 SE SE7116475A patent/SE412064B/xx unknown
- 1971-12-22 IT IT54935/71A patent/IT945597B/it active
- 1971-12-23 CA CA130,993A patent/CA969547A/en not_active Expired
- 1971-12-23 IE IE1643/71A patent/IE36678B1/xx unknown
- 1971-12-23 GB GB6011371A patent/GB1374800A/en not_active Expired
- 1971-12-23 GB GB3830273A patent/GB1377469A/en not_active Expired
- 1971-12-23 GB GB3809473A patent/GB1375157A/en not_active Expired
- 1971-12-24 BE BE777250A patent/BE777250A/xx unknown
- 1971-12-24 AU AU37333/71A patent/AU465099B2/en not_active Expired
- 1971-12-27 AT AT1113071A patent/AT312598B/de not_active IP Right Cessation
- 1971-12-27 DK DK634871AA patent/DK139385B/da unknown
- 1971-12-27 AT AT163873A patent/AT318608B/de not_active IP Right Cessation
- 1971-12-27 IL IL38452A patent/IL38452A/xx unknown
- 1971-12-28 NL NL7118000A patent/NL7118000A/xx not_active Application Discontinuation
- 1971-12-28 DE DE19712165021 patent/DE2165021A1/de not_active Ceased
- 1971-12-28 ES ES398379A patent/ES398379A1/es not_active Expired
- 1971-12-28 YU YU3284/71A patent/YU35001B/xx unknown
- 1971-12-28 CH CH138073A patent/CH556342A/fr not_active IP Right Cessation
- 1971-12-28 AR AR239854A patent/AR201728A1/es active
- 1971-12-28 CH CH197073A patent/CH554873A/fr not_active IP Right Cessation
- 1971-12-28 CH CH1905071A patent/CH558366A/fr not_active IP Right Cessation
- 1971-12-28 FR FR7147107A patent/FR2121020A5/fr not_active Expired
- 1971-12-28 DE DE19712166996 patent/DE2166996A1/de not_active Ceased
-
1973
- 1973-10-18 SU SU1966487A patent/SU535905A3/ru active
-
1974
- 1974-01-04 AR AR251821A patent/AR196969A1/es active
- 1974-05-15 SU SU2133311A patent/SU535908A3/ru active
-
1975
- 1975-05-15 SU SU1732630A patent/SU541436A3/ru active
-
1978
- 1978-12-11 YU YU2895/78A patent/YU35256B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES398379A1 (es) | 1975-06-16 |
| SU535905A3 (ru) | 1976-11-15 |
| IE36678L (en) | 1972-06-28 |
| IT945597B (it) | 1973-05-10 |
| ZA718532B (en) | 1973-08-29 |
| DE2166996A1 (de) | 1977-05-18 |
| IE36678B1 (en) | 1977-02-02 |
| YU328471A (en) | 1979-12-31 |
| AT312598B (de) | 1974-01-10 |
| GB1377469A (en) | 1974-12-18 |
| GB1375157A (enExample) | 1974-11-27 |
| BE777250A (fr) | 1972-06-26 |
| CH558366A (fr) | 1975-01-31 |
| NL7118000A (enExample) | 1972-06-30 |
| YU35256B (en) | 1980-10-31 |
| DE2165021A1 (de) | 1972-10-12 |
| AR196969A1 (es) | 1974-02-28 |
| SE412064B (sv) | 1980-02-18 |
| DK139385C (enExample) | 1979-07-30 |
| FR2121020A5 (enExample) | 1972-08-18 |
| IL38452A0 (en) | 1972-02-29 |
| AR201728A1 (es) | 1975-04-15 |
| AT318608B (de) | 1974-11-11 |
| SU541436A3 (ru) | 1976-12-30 |
| YU289578A (en) | 1980-04-30 |
| SU535908A3 (ru) | 1976-11-15 |
| CH556342A (fr) | 1974-11-29 |
| CA969547A (en) | 1975-06-17 |
| IL38452A (en) | 1975-04-25 |
| CH554873A (fr) | 1974-10-15 |
| AU3733371A (en) | 1973-06-28 |
| DK139385B (da) | 1979-02-12 |
| YU35001B (en) | 1980-06-30 |
| AU465099B2 (en) | 1975-09-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |